


Logged In

by Talesmaniac89



Category: Supernatural
Genre: Chatting & Messaging, Dean Fluff, Dean Winchester Fluff, Eventual Fluff, F/M, Fluff and Humor, Mutual Pining, Not Actually Unrequited Love, Online Relationship, Online Romance, Pining
Language: English
Status: Completed
Published: 2020-08-12
Updated: 2020-08-12
Packaged: 2021-03-06 05:21:31
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 23,046
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25858096
Author URL: https://archiveofourown.org/users/Talesmaniac89/pseuds/Talesmaniac89
Summary: Sam tells Dean and the reader about a new online community for hunters and they both scoff at him, but secretly use it and end up drawn to each other.
Relationships: Dean Winchester/You
Comments: 9
Kudos: 55





	1. Chapter 1

“You found it where?” 

The question came out as more of a barked laugh as Dean threw his brother a quizzical look that mirrored yours over his raised beer bottle. You were enjoying a post hunt celebratory beer when Sammy let it slip where he’d found the last bit of day-saving info that got you your monster.

“I told you, I was talking to this hunter from Arizona online and…” Sam started parroting his earlier words over Dean’s laugh as you both looked at the younger hunter with a mix of shock and amusement. 

“Yeah, yeah… But a forum? There’s really a hunter’s forum online? What’s next, Tinder for demons?” You asked, your words only making Dean laugh harder as the younger hunter threw you both one of his trademarked bitchy glares.

“It’s not a forum, it’s more like an information sharing channel where you can chat with other hunters,” Sam said, standing up for the service that had saved your lives, not matter how silly it sounded to you.

“So it’s a chat then? Like… Lol, brb, just need to gank this monster real quick,” You threw the words back at Sam with a shit-eating grin, earning you another wink and a laugh from the older hunter that made your heart jump in your chest. _Yeah_ , you really liked making Dean Winchester laugh, even if poor Sammy got the bad end of the deal. 

Still, you did find the whole idea of a hunter’s chat kind of silly. What happened to the days where you had to rely on wit and phone calls to survive a hunt? Maybe you were just being overly sentimental, but you doubted all the info you could get online was as reliable as some good ol’ fashioned research.

“No (Y/N), it’s just a place to share info with other hunter who might have hunted the same thing before. A place to get tips and tricks and…” Sam started, the big guy clearly not knowing when to give up. Hell, by now you were just pulling his leg as you smiled into your beer bottle. 

Sure, the site had saved your asses, but… Sam was your best friend, he was like a brother to you. And what sister didn’t enjoy annoying her brother? Alright, so, the service, from what Sam had told you before the ribbing started, seemed reliable and like an alternative way of finding info and getting to know other hunters, but that didn’t mean you had to completely buy into the idea. Especially not when you could annoy your techie best friend for a while. 

“So… Demon pinterest? Big baddie reddit? Ooooh! I know, I know! Hunter’s wikipedia!” You said, grinning at the frustrated younger Winchester as he rolled his eyes at you.

“(Y/N)…” Sam sighed your name over Dean’s barked laughs as you softened your smile into something sweeter. 

“Yeah, yeah Sammy. Sorry, I know it saved us. Thanks,” You said, raising your bottle to touch the neck of it against his and stopping your teasing of the other hunter before he rolled his eyes so hard at you that they got stuck in the back of his head. 

“But that doesn’t mean I have to completely buy into it,” You added, still not fully sure about the service Sammy had been raving about before the teasing started.

“Yeah, you never know who’s on the other side, could be some kid thinking it’s all just role playing. Y’could end up with bad info,” Dean agreed with you, taking on a big brotherly tone, as if he was admonishing his kid brother about internet safety and stranger danger, though Sam clearly could take care of himself. 

“Books seem safer, you can rely on ‘em. And when they fail you, Bobby’s just a phone call away,”

“Actually, it’s invitation only. Only hunters can access the site, and only after being invited by someone else. Garth gave me the invite,” Sam said, still sticking up for the service though he had to know it was a lost cause with only two technologically challenged hunters in his audience. 

“I’m just sayin’ don’t knock it till you’ve tried it,”

“No thanks,” You scoffed into your beer, adding a small involuntary shiver at the thought of relying on anything other than the books and hunters you trusted. You risked your life out there, and worse, the life of your best friend and the man you kind of, maybe, ok, _definitely_ had a thing for. 

You couldn’t trust anything other than absolutes and the internet was a grey zone in a still unidentified shade of grey. You didn’t want to take any chances when it came to the precious family you’d finally made for yourself after years spent alone on the road.

“Well, I’ve sent you both invites. Just in case you change your mind,” Sam said, his triumphant smile making it seem as if he was sure you’d try it out and love it, though you doubted either of those things would ever come true.

“Thanks, but no thanks”,” Dean shot in, making you chuckle into you beer as you finally moved away from the idea of Hunter Net or whatever the hell the idiotic page was called and onto other subjects, like the always fun breakdown of your latest hunt and more beers to celebrate surviving said battle.

—

Still, it was only a few nights later that boredom and curiosity got the best of you. You’d been reading up on some monsters, passing another quiet evening in your bedroom in the bunker with a mix of random YouTube videos and actual research in actual books when you checked your email in hopes of finding some random spam mail to relieve your boredom and saw the invite to the forum, chat, all things insta-hunt, that Sammy had sent you. 

And honestly, though you still really believed the whole thing was a bunch of bull crap, you still couldn’t fight your curiosity as you looked at the email in your inbox. After all.. A look wouldn’t hurt. It didn’t mean you actually had to use it for hunts. Or take it all that seriously.

Sighing to yourself you sat up a little straighter and clicked on the link. Sammy didn’t need to know. Hell, if he found out he’d probably give you that annoying smug ’I told you so” look, so it was better if he didn’t know. You’d just have a quick look at what it actually was, since Sam’s explanation had been… Lacking. Then you’d put it back down and rely on your books and the contacts in your phone again. 

The internet was fine for entertainment and the occasional look at local and international news outlets. There was no way this page would make you see it as a possible information sharing channel when it came to your “job” as well.

Waiting for the page to load you cast a quick look towards your closed bedroom door. Hell, if anyone saw you, they’d think you were about to look at porn instead of just visiting a more or less innocent online chat/forum page reserved for hunting all things bad and nasty. However, you lived with two hunters who not only were just as likely to tease you as you were them, but who also had no real idea of what privacy was. 

A quick look. That was all. Looking back at your laptop screen you watched the page finish loading, which took forever on your crappy WI-FI and ancient laptop combination.

—

Ok… 

You had to admit that your first look had turned into a bit more that just a quick in and out of the page. Sammy had clearly stumbled onto something a bit more useful and a bit less “Tinder” or online role playing network than you had at first expected. The page didn’t only have a forum and chat function, but also an extensive library filled with digitized copies of books that weren’t present in the Men of Letters library and even a sort of news bulletin where people could share cases they’d fallen across, but were too far away from to deal with themselves. 

The page’s algorithm also seemed to automatically screen the world wide web for the weird and unexplainable and add cases of interest automatically to the news bulletin.

So you ended up actually using the page quite a bit during the evenings after making a strategic retreat to your room. Sure, you double, even triple checked the information, but everything seemed to check out. Of course you would never tell Sam and Dean that you were using it. No, you’d rather spare yourself from that, but you couldn’t make yourself just look away from what seemed to be an actually useful tool either. 

Though you had only used the directories or read some posts. You’d stayed away from actually posting yourself or even entering the chat area where you could “connect” with hunters from all over the US of A.

Still, that evening, as you closed the door behind you and jumped online into another evening of geeking it online with the other www hunters, things took a turn for the possibly worse quite early on.

You had just logged in with your more or less inconspicuous Warrant themed username when the little icon in the corner of the grey and white hunter page blinked. It had happened once or twice before that the little icon that signaled a private message had blinked and you normally just checked and ignored the message from whatever hunter it was that wanted to network.

Yet, somehow you found yourself actually entertaining the idea of a conversation for once as you opened the window and saw something other than the “Hello, I hunt in xxx, let’s be best buds and have rainbows shoot out of our asses”-messages that you had seen every single time before. 

Alright, so _maybe_ your mind embellished the usual message a little. Whatever… Didn’t make ‘em any less annoying. 

—

> **JustTryingItOut:** _Yours is the first username without hunter, a weapon or something in Latin in it. So I just felt the need to reach out and tell you that Warrant is not only awesome, but that no matter how overplayed Cherry Pie is, it’s still awesome._

The message blinked on the screen, black letters on a white background, with the uninventive username somehow making the message seem funnier than it actually was. And though you couldn’t put your finger on why, you found yourself typing your reply to one of the private messages you received for the first time ever. 

> **CherryPie:** _Back at ya “JustTryingItOut”, and I don’t know where you’re from, but where I’m from Warrant is only overplayed ‘cause I’m playing their albums on repeat and hell, that’s fine by me._

Sending the message, you grinned at the screen, stopping only to put in your headphones and doing exactly as your message stated, putting your trusty rock playlist on shuffle before quickly adding to your message to the stranger on the internet.

> **CherryPie:** _You, however used awesome twice in one sentence, which is way more repetition that I am comfortable with._

> **JustTryingItOut:** _Hey don’t knock awesome. Awesome covers everything I need it to cover._

Allowing yourself a small chuckle at words you could picture leaving a certain hunter you knew that resided just a few rooms down from you, you shook your head at the screen. Resolving yourself to stop the conversation in its tracks before “JustTryingItOut” could keep you from checking out that book on shifters you’d been planning on scanning through on the page.

> **CherryPie:** _Yeah, yeah…. I believe ya. But, look… I don’t use this page to actually talk to people. I don’t like doing that in real life, and online is no different. So… See ya when, or if, I see ya I guess._

As soon as you’d typed the words, you closed the little IM window and moved your cursor to enter the website’s extensive archive. Yet, before you could even click on the correct menu option the little box was back with a vengeance, blinking to alert you of a new message.

> **JustTryingItOut:** _Neither do I…_

> **JustTryingItOut:** _Use this as a way of talking to people I mean._

> **CherryPie:** _Could’ve fooled me._

Rolling your eyes you resolved yourself to wait for the other hunter’s response since they didn’t seem to give up all that easily. 

> **JustTryingItOut:** _No, really. I just joined cause I was curious, and kinda stayed around ‘cause it wasn’t as bad as I thought it’d be._

Sure… You could kind of recognise yourself in that situation, but… You weren’t the one who’d initiated conversation. And honestly, you were fine with the page staying as a digitized archive of books you didn’t have in your collection. Nothing more, nothing less. 

This hunter however, seemed to want to try every aspect of the page.

> **CherryPie:** _And yet, here you are, blowing up my IM. What changed Mr. JustTryingItOut? I’m guessing with the Mr. btw… Most people in our business are men and judging by your oh so creative username I’m guessing you’re a man among men._

> **JustTryingItOut:** _And based on that I just know you’re a lady._

You scoffed loudly at your computer, fully focused on the IM window now as you raised an eyebrow at the man’s choice of words.

> **CherryPie:** _Awh lady… No one calls me a lady sweetheart. Not when they know me. I’m a woman, but I’m definitely no lady. Or at least I’m a “lady” that could probably kick you ass in two seconds flat._

> **JustTryingItOut:** _Ouch… But no, all joking aside. I had a very good reason for actually talkin’ to you…_

You’d been set for a bit of a quick back and forth where you effectively turned whatever testosterone was on the other side of the screen to a useless pile of dust, so the quick change in conversation and pace caught you a bit off guard. Not that you hated it. 

You enjoyed a quick paced conversation, especially one that changed it up. It was a bit of an occupational hazard. Everything went fast in your world, and when someone couldn’t keep up it just annoyed you. 

Letting go of all the quick comebacks you’d lined up, you instead just wrote the question Mr. “JustTryingItOut” seemed to be waiting for.

> **CherryPie:** _Yeah? And what might that reason be?_

> **JustTryingItOut:** _I’m bored outta my mind._

Boredom… The only real reason to ever engage in conversation with a complete stranger online… Yeah, you got that. Actually, as you glanced once more at the archive menu you realised that you were pretty bored yourself… 

And hell, at least this “JustTryingItOut”, whomever he might be, was more interesting than “20 possible new ways to use wolfs-bane” or “The complete history of shifters and changelings”, which had been on the agenda before he so rudely interrupted your studious ass.

> **CherryPie:** _You know what…. I think I might be a bit bored myself…_

—

After the first chat, where half the night was spent in an animated discussion about the best classic rock bands, and where you had totally schooled him in the intricacies of English punk, your talks with JustTryingItOut became an almost daily occurrence. 

You kept telling yourself it was only a way to stave off the boredom between hunts, or avoid watching Dean flirt with some random girl at a local bar. But honestly, you found yourself looking forward to the conversations you had with J.T as you’d started calling him, because JustTryingItOut was a fucking mouthful and you were a lazy typer. 

You’d barely made it back from another hunt and shared a glass or two with the boys in the library before you retreated into your little cave and turned on your laptop once more. Dismayed to not see your regular chat buddy online, you resolved yourself to check out if any new cases had been added to the feed. Though you still felt the effects of the few whiskey’s you’d shared with the guys and really couldn’t be bothered to do any actual reading. Still, hell, you felt better in fooling yourself into believing you were actually reading, instead of just waiting for J.T to come online.

You luckily didn’t have to wait long, though you of course still believed you hadn’t been waiting at all. Almost as soon as you’d started reading through a less than informative post about a hunt in Alaska, that you had no way of helping out with anyway, you saw the now familiar blinking of an incoming message in the corner of your screen. 

> **JustTryingItOut:** _Are you ever not online? Sometimes you make me doubt you’re actually a hunter Cherry… Are you sure you’re not really just an old, balding man in a basement somewhere?_

> **CherryPie:** _Hey, rude! I actually just got back from a hunt and haven’t been online for days in case you haven’t noticed my absence. Which you should’ve noticed by the way… I. Am. Amazing._

> **JustTryingItOut:** _Same, actually. The back from the hunt part I mean… Not that I’m not amazing… Had to crack a hard one out of state with her._

You cringed in shared pain at J.T’s words. Over your many discussions you’d at times strayed a bit too close to what Dean would call “chick flick talks” as you both bemoaned the unrequited crushes you both somehow had to hunt with.

Hell, sometimes you wondered if J.T wasn’t just you with a dick. You were both still pretty cynical about the whole damned page and the hunter’s life, hunting was everything, and yet there was that one person in both of your lives that somehow mattered more than all of that.

For you that person was Dean, though to J.T Dean was better known as ‘him’, and to J.T it was ‘her’. The two untouchable people in your respective lives that were close enough to touch, yet somehow way out of your reach.

> **CherryPie:** _Damn, I feel you. He was with me as well. The hunts are never bad. We have to focus during them. It’s just after…_

> **JustTryingItOut:** _I know what you mean. The dive bar celebrations. The other people that are never you…_

J.T’s words hit home as you recognised yourself in them. Maybe that was why you didn’t mind sharing with him. Sure, lately you found your time spent daydreaming split equally between the two male hunters that occupied most of your thoughts, but that didn’t mean Dean’s flirty ways didn’t still sting.

Though you knew you shouldn’t really like either Dean, nor the internet stranger J.T, you somehow couldn’t stop thinking about either. Of course, since you didn’t actually know what J.T looked like, in your mind you were actually fantasising about a mix of Jake Gyllenhal and Chris Pine when you thought of him. 

So your mind was a confused mix of Dean and your Chris Gyllenhall aka J.T. Though you’d never admit to liking either, not even if someone tried to torture the information out of you. Hell, they’d especially never learn of the dirtier daydreams involving yourself, Dean and your J.T mix of Gyllenhal and Pine… No, those dirty thoughts you were taking with you to your grave.

> **CherryPie:** _Yeah, though this time wasn’t all that bad. He left the bar with us. Not with some bartender or blonde college girl with daddy issues._

> **JustTryingItOut:** _I wish I could say the same…_

Part of you winced at his words, as if it was Dean walking out of a bar with his arm casually slung around the shoulders of another woman, yet…. Another part of you, an awful ugly part, somehow rejoiced that J.T and his girl hadn’t gotten together. Damn, this internet thing was really messing with you. Though you knew you liked Dean. You had for years. Part of you also felt attracted to J.T…

Somehow, over your many conversations, your heart, which you thought would always belong fully to Dean, had become as tangled as the earbuds you were using to listen to your playlists whilst chatting online with your internet stranger… 

J.T was so like you. And maybe it was only that… Maybe you saw yourself in him and felt closer because of it… But it still felt like something else. Something more. 

Yet, you made sure not to show that ugly part of yourself as you typed your response to the man waiting somewhere across the many layers of pixels, wires and ones and zeroes that made up the internet.

> **CherryPie:** _Shit, I’m sorry man…. I thought she never left with anyone?_

> **JustTryingItOut:** _No… She still didn’t hook up with anyone, but there was this guy. He was… Pushy._

> **CherryPie:** _A man being pushy is pretty much commonplace in the bars hunters normally frequent… Trust me._

Just as you’d somehow gotten used to your newly split feelings and your nearly nightly conversations with J.T, you’d also gotten used to noticing the same things he confessed to feeling and experiencing in your own twisted unrequited love life. Him, like you, seemed to notice everyone that looked in the direction of the person he liked. 

You’d basically perfected the art of knowing exactly which woman would come up and talk to Dean over the years. Yet, where you held it in, J.T seemed to have another approach. Though he never seemed to actually do anything to ruin a poor guy’s chances if she seemed interested.

> **JustTryingItOut:** _No, he made her uncomfortable. Didn’t know when to give up. And yeah… Before you say anything Cherry, I know she can handle herself. She could probably have kicked my ass and the douchebag’s without breaking a sweat._

> **CherryPie:** _And she’d do it in heels._

> **JustTryingItOut:** _Damn right she would! Still though… He pissed me off, he pissed her off.. He was touchy and idiotic enough for all of us to react._

Cringing you thought back to similar situations. Unfortunately there were too many to count… Even during your latest hunt celebrations there was an asshole who wouldn’t take no for an answer. Though in your case the bastard had left you alone all of a sudden after very little urging to fuck off from you. Sometimes having to guys with you at all times really paid off. Guys seemed to back off when they realised they weren’t the only alpha in the room.

> **CherryPie:** _So what did you do?_

> **JustTryingItOut:** _I wanted to use my whiskey and lighter combo to set his damn ass on fire. Everything about him seemed greasy enough to catch of fire in a second flat. But… Unfortunately I didn’t do it…_

You caught yourself laughing out loud at the thought of some greased up douchebag running around whatever dive bar J.T had been to on fire. All whilst she looked on in complete and utter shock and horror. Stopping your laughter you lowered it to a chuckle to keep your housemates from thinking you were actually losing your mind, before typing a short answer to J.T. 

> **CherryPie:** _Why not? It would’ve been hilarious!_

> **JustTryingItOut:** _Hell yeah it would’ve been. But, y’see… There’s this little problem of arson being a felony and the douchebag not being the monster of the week. So… Being the bigger person, I backed off and kept away from the flammable liquids._

> **CherryPie:** _Kudos to you… I would’ve probably lit the bastard on fire and used him to roast some peanuts to go along with my next few drinks._

> **JustTryingItOut:** _One day you’ll learn to temper those urges young padawan. Like I have._

You grinned at the screen as you let your fingers fly over the keyboard. Even with your mixed emotions and split feelings you still loved these moments. The little back and forward quips and jokes you shared with the stranger online were a welcome break from hunting and preparing for the next hunt. They were to you what meditation was to others. A much needed break from reality…. And somewhere, deep down, you just knew you were the same to J.T, no matter where in the great big U.S he resided. 

> **CherryPie:** _Oh suuuure, Mr. Enlightened over there. I’m sure you didn’t just let it go._

> **JustTryingItOut:** _Hell no, I cornered him and told him to keep his hands and eyes to himself since it seemed to annoy her as well. I might even have showed him the sawed-off I used during the hunt. BUT! I didn’t set his stupid looking skinny jeans on fire. So I think I deserve some praise for that._

Smiling to yourself, you pictured what you had come to see as your mix of Gyllehall and Pine cornering a guy with poorly veiled contempt as he told him exactly where he could fuck off to with a smile on his face and a whiskey in his hand. 

> **CherryPie:** _Haha! I bet he pissed his pants!_

> **JustTryingItOut:** _He didn’t, unfortunately… But he sure as hell looked like he was about to._

> **CherryPie:** _Awesome!_

> **JustTryingItOut:** _Hey, I thought we talked about this? That’s MY catchphrase, you have to get yourself one of your own._

Grinning, you settled in for another night of back and forth with another man you knew was completely out of your reach as you responded back to his remark with a quip of your own which you knew was sure to set him off. Knowing fully well that your constant mockery of the word “awesome” always seemed to grind J.T gears.

> **CherryPie:** _It’s a free world dude._

—

Ok, so you were in deep. 

You couldn’t even lie to yourself about it anymore. Hell, if whichever techie hunter that’d set up the page decided to earn a quick buck by making the page a paid service you’d probably pay to keep using it. Though Dean was still taking up majority of the space in your heart, your internet stranger was taking up most of your time. 

Which was just as good, since Dean as well had started spending his time in his room researching. With three, or actually two since you were a dirty little liar, study bugs who spent the evenings researching the bunker was the most unsociable place on earth as of late.

Not that you noticed, as you spent evenings until early mornings chatting with J.T and ending up sleep deprived throughout the day. It was becoming a necessary part of your evening. And soon your chats started turning away from her and him to flirtier subjects. Your own conflicted feelings constantly pushed aside as you indulged in the harmless flirting.

Sure, you knew both of the men filling your head with both dirtier and innocent daydreams were out of your reach, either by distance or emotionally, but you couldn’t make yourself give either up. So, like so many evenings before, you found yourself sitting up in bed, with your laptop on your lap and chatting away with J.T, though the sun was soon about to rise.

> **JustTryingItOut:** _Damn, how are you still awake? Or is it even late there? It’s almost morning here._

J.T interrupted your ongoing debate about where to find the best pies in the great U.S after probably looking at the clock on his screen and seeing how late, or early it actually was. 

His comment made you look down and grimace at the time displayed on your own screen as well in case it was just a time difference thing, though you’d kinda figured you were close enough to not have much difference in time, nearly 5 am. 

Yeah, you were going to suffer in the morning. Still, instead of doing the smart thing and turning in for at least a few hours of shuteye you instead found yourself responding in kind with a small smile.

> **CherryPie:** _Says you! I’m not the only one up! And yeah, nearly morning here too. Doesn’t matter to me though. I’m basically fully fueled by caffeine, sarcasm and dirty thoughts._

> **JustTryingItOut:** _You must run out at some point, I’m about ready to crash._

> **CherryPie:** _Nah… It’s a form of renewable energy, but I’ll let you get your beauty sleep._

You felt the familiar pang of loneliness you always felt when saying good night to the hunter on the other side of the screen, as you got ready to do your usual sign off and try to get a bit of sleep yourself. Still, as his answer appeared in the little chat window you threw away all ideas of sleep and smiled at the little letters. 

> **JustTryingItOut:** You know what… _No thanks, I’d rather stay here talking to you._


	2. Chapter 2

Days turned to weeks and weeks turned to one month, then two, as you spent most of your evenings and nights when in the bunker talking to J.T. The conversation going from flirty, to serious, to weird and then back to flirty again fast enough to give anyone a whiplash. The flirting, among other things, only upped as time passed. With both J.T and you having equally sharp wits and dirty minds, your conversations were always interesting. If not always PG.

Somehow you never had to wait long when you logged in and he wasn’t online. It was almost as if he could sense you waiting. Though hell, you’d never admit that you were waiting. Even if you weren’t using the page for much except speaking to J.T anymore. 

And as you dropped, not all that gracefully, down on your bed after another long day of research J.T once more proved to you that he could somehow read your mind through the many layers of internet that separated you. Coming online mere minutes after you logged in and started browsing the news bulletin. The little notification popping up on your IM window easily pulling your attention away from a case you knew Bobby had a man on as you unsuccessfully tried not to smile at the idea of spending another lazy evening chatting with your online stranger.

> **JustTryingItOut:** _Ok… I’m genuinely starting to think you’re always on here Cherry. Are you sure you’re not some old man in a basement just listening to Warrant on repeat?_

You chuckled at the “concern” that you had both thrown back and forth at each other time and time again. Hell, it had almost become your standard greeting, slipping from the fingers of whomever logged in last as easily as the more common “Hi” did for others. A smile easily formed on your lips as you typed your reply.

Talking to J.T like that, just joking and having fun, somehow made you feel like you had a stomach full of butterflies, yet at the same time it completely relaxed you and made you feel at ease. Teasing easy smiles from you that you normally hid to look strong and in control. Smiling wasn’t a sign of weakness, but some of the older hunters tended to see it that way. Especially if the smile came from you instead of one of your male counterparts.Sons of bitches all of ‘em, but it still made you smile less. J.T and the Winchesters, however, easily broke that little humourless wall around your life. Brought out the girl behind the bitch face so to speak…

> **CherryPie:** _Hey! Don’t you go starting that again! You’re always online too. How do I know YOU’RE not the basement dweller?_

> **JustTryingItOut:** _Well.. Who knows? Maybe we both are. And damn, if that’s true then we’re the awesomest basement dwellers ever._

You cringed slightly as he butchered the English language. Knowing full well that he only did it to annoy you. Just like how you kept flip-flopping back and forth between making fun of his use of awesome and stealing the word he considered _his_ from him. This time it was definitely going to be the former though.

> **CherryPie:** _Awesomest is not a word J.T… Actually, I refuse to believe that even “awesome” deserves the status of a word. It’s a disgrace to dictionaries everywhere to have the word inked within their spines. Like a tattoo you get whilst drunk. Just… Awful._

> **JustTryingItOut:** _I take it back… I’m the awesomest. You’re just mean._

You laughed out loud as you read J.T’s reply. Picturing your Chris Gyllenhaal mix pout along with the words just making the whole thing 20 times more adorable as your heart did little flips in time with your laughter. Damn it, how could he be all hard, steel and hunter one second and the next be a damned fluffy frickin’ bunny? It was unfair, your poor heart couldn’t keep up half the time. Yet you never wanted him to slow down.

Reeling back the laugh, but letting it continue to shine in your (Y/E/C) eyes you refocused on the screen, already ready with a reply. Because, hell, that’s just who you were. As in, awesome… Even though you mainly hated the damn word, that was definitely who, and what, you were. And maybe, possibly, what J.T was too. Though you’d never tell him that.

> **CherryPie:** _Awh, did I hurt the clever pie’s feelings?_

> **JustTryingItOut:** _?_

> **JustTryingItOut:** _Clever pie?_

Smirking you waited a beat before turning on the flirt. Easily turning the conversation on its head with just a few quick taps on your keyboard. Yeah… These nights were definitely more fun than researching or lying awake pining after Dean. As long as you kept your mind away from Dean, and the guilty thoughts that followed. Fuck… Yeah, now you were thinking about Dean again… Shaking your head, you brought back the little devil on your shoulder before hitting the enter button and sending your tiny pixelated, and not so innocent love letter, disguised as an explanation, across the many layers of WiFi, screens and connections.

> **CherryPie:** _Yeah…. Like Smart cookie, but… Y’know, tastier._

> **JustTryingItOut:** _Ok, you’re forgiven, and pretty fucking amazing._

—

There were of course evenings and night reserved for the two other men in your life too outside of hunts. Like the movie night that had made you tell J.T you had plans and wouldn’t be online the night before, or more like that morning, when you signed out. You love your movie nights with the Winchesters. They had the best, worst taste in movies and all the cringiest comedies, the loudest action movies and the least scary horrors all available within the four walls of the bunker.

So as you walked down the hall, (Y/H/C) hair still damp from your shower, you looked forward to your internet free evening with the two hunters. Even though guilt gnawed at you like you were some cheating housewife these days around a certain hunter. Hell, you technically had no reason to feel guilty. Your love for Dean was as one-sided as it could possibly get, yet the feeling still snuck in.

Though deep down you knew the guilt was mainly internal. It was guilt for believing only Dean could make your heart beat faster, yet constantly betraying that belief when your mind strayed from Dean’s green eyes to the more or less imagined image of the J.T celebrity mixtape that played on repeat in your mind. It was due to your own current mixed feelings, betraying your earlier belief that you’d be steadfast in your love, unrequited or not.

Still, you couldn’t deny the fact that you still loved Dean. Not when being near him made your heart beat like a bass drum and made you feel like you were flying and falling all at once. Not when just seeing him smile in your direction from the couch made you consider going to lie down for a second due to your own stupid lightheadedness. Damn that man was sin personified. Dressed in jeans and flannel and served with a generous portion of oh-god-the-things-I’d-do-to-you.

“Long time no see stranger,” Dean’s tone was light and teasing as he scooted over on the couch, making room for you before offering you one of the beers awaiting your arrival on the table. It felt as if you hadn’t seen the older hunter’s easygoing smile in days, or possibly weeks, as you let yourself drop down into the couch with a quick eye roll and a smirk.

“Like your studious ass can speak. Sammy and you’ve been constantly busy too, so it’s not just me,” You said, mentally crossing your fingers behind your back at your tiny white lie, since technically you _had_ been busy… Busy stretching your underused innuendo muscle and letting your dirty mind loose on the internet. 

“Tell me the truth Winchester… You’re living a second life behind our backs. Hunter by day, superhero by night?” You raised an eyebrow at Dean, pretending to scrutinize him with a smile. Yet the smile on your own lips dropped slightly as you saw Dean’s waver behind his raised bottle. 

“I wish, I’m all about that research lately, Batman 2.0 will have to wait. No matter how much Cat Woman wants to get her claws in me,” Dean said before drowning anything that could have followed his flat joke in a generous sip of beer. 

That… That was something you hadn’t been missing when you were in front of your laptop at night. Dean had been acting strange lately. He was distant, and lost in thought. Hell of course you’d often found the hunter “distant” due to your own unrequited feelings, but lately it had been clear enough for even Sammy to send you questioning looks that you could do nothing but return with a shrug.

It almost seemed like the hunter was hiding something from Sammy and you. Though, you weren’t really one to speak, all things considered. So instead you safely navigated the conversation back onto safer topics and even managed a smile and an eyeroll at Dean’s lame joke. 

“So, what are we watching tonight, and please tell me it’s cringey as fuck. I need something cringey right about now,” You asked, sinking further down into the worn couch and pulling your legs up to make yourself comfortable before refocusing your attention on the still blank TV screen. Not that, that helped you keep your eyes off of Dean, since you still saw his reflection next to yours through the darkened TV. 

“I need to judge somebody’s choices, since I’ve been unable to judge my own lately. What’s a hunter to do without hunts and bad decisions?” You added, still loving the feeling you got when you managed to tease a barked laugh out of the older hunter. Which Dean willingly offered at your words and movie wishes. 

“Wow, (Y/N),” Dean laughed back, nudging your shoulder with a loose fist and turning your full attention back towards him and those damned shining green eyes. Damn him and those eyes, they sent you flying headfirst down into vertigo land faster than any roller coaster ever could. “What happened? Back in the good ol’ days you still swore you had great taste in movies and that we’d never ruin it. Yet, here you are, loving the cringe,” He punctuated his sentence with a small head shake dripping with mock disappointment in a way that made you roll your eyes at him like some bratty teenager.

“Ah yes… _Those_ good ol’ days. I remember them,” You sighed, laughter still evident in your voice as you stopped to smile at Sammy sitting down in the chair next to the couch. “Back then I was sweet, innocent and all rainbows, cotton candy and unicorns… Shit happened after that,”

“(Y/N), you were definitely not innocent when you met us,” Sam shot in, easily joining the easy banter before the traditional Men of Letters movie night whilst reaching for a beer.

“Hey I was… Well, at least _one percent_ more fluff and softness than I am today,” You shot back in mock offence. Stopping only to take a generous sip of your beer before underlining your own imagined earlier innocence. “ _At least_ … If not more!”

“You were in the middle of decapitating a fang… With a crowbar you shoved in under his jaw line,” Dean’s words and laughter easily brought back memories of what was probably the grisliest meet cute moment ever. And possibly one of your most creative and proudest moments as a hunter. 

“Exactly! Like I said, so innocent. Now I just use fire and machetes. Ah, the folly and creativity of youth,” You shot back with a grin and a wink. Your words having the desired effect as Dean laughed whilst your best friend shook his head in the direction of you and his big brother. You usually based whether you had successfully made a fool out of yourself on Sammy’s headshake. The more the mop of brown hair on the younger hunter’s head moved, the better the joke.

“Just admit it (Y/N), you swore up and down you’d never like our movie choices. But you love ‘em now,” Dean said with a chuckle, still trying to get you to admit you loved the cringe. But, just like you’d never admit to loving the hunter beside you, with his stupidly cute yet blindingly handsome crooked smile and teasing eyes, you would also never admit to being wrong when it came to their movies. You had your pride, and a healthy dose of excessive stubbornness after all.

“Just turn on the damn movie, pass the popcorn, and shut up Winchester,” Putting down your empty bottle to grab a new one you stuck your tongue out at Dean and shoved Dean’s booted feet off the table with your own like a real mature adult. 

Returning Dean’s eye roll with a smirk of your own as you curled your legs up under you once more, you got ready for a night of drinks, popcorn and movies so bad they were good. All enjoyed together with two of your favourite people in the whole world.

— 

Two movies and several empty beer bottles and a _few_ shots of something stronger, later you were stumbling back into your bedroom. Happy, yet conflicted from an amazing night together with your crush that probably saw you as nothing more than a good friend and an even better hunter. The alcohol didn’t help your conflicting emotions, and honestly… It also didn’t help your impulse control. Almost as soon as you’d stumbled through your door and onto your bed, you had your laptop booted up and next to you.

You hadn’t planned on going online. Hell, you even told J.T you weren’t coming online that night at all. But, just like drunk people texting their exes at 2-3 am on a Saturday night, your drunk ass decided to go online. ‘Cause clearly alcohol was the best cure for making mature, healthy decisions. It erased that little voice in the back of your head in two seconds flat.

Hell, you weren’t going to stay online long. Not when the room was spinning and the letters on the screen refused to stay completely still. You just… Needed to say hi, and bye. And possibly a few words in between before getting your sexy, alcohol infused body to bed. It was weird really… Sammy was your best friend, and Dean was the man you loved. Yet J.T somehow seemed to slowly but surely gain a place in your heart as a mix of both those things the more time went on. And so, going to bed without saying good night to him just didn’t feel right.

Luckily, or unluckily considering how drunk you were, for you, J.T seemed to already be online as you somehow managed to log yourself in and navigate your way down to the little IM chat window with one eye closed to stop the letters from dancing on the screen.

> **JustTryingItOut:** _I thought you weren’t planning on coming online tonight?_

Seeing J.T’s name beside the message, or at least his very uncreative username, made you smile like a freaking schoolgirl as you made yourself comfortable on your bed and rested the laptop on your stomach. Yeah… Talking to him was just what the doctor ordered. Even your eyesight seemed to stop doing that annoying thing of jumbling the letters together by seeing his message.

> **CherryPie:** _Of course I’d come online! Talking to you is kinda my favourite part of the day these days._

> **CherryPie:** _After eating… And having a beer. Oh! And kicking ass when I spar with the guys… Alright, look… You’re definitely in the top five._

You giggled a little at your own stupid joke. Because, hey… You were drunk. And even hunters giggled after God knows how many shots and beers. You swore it was written in some magical hunter’s rule book. Somewhere in the same section that allowed you to be able decapitate a fang from across a room some days, yet at the same time fall flat on your face whilst standing completely still other days.

> **JustTryingItOut:** _I’m honoured…_

> **JustTryingItOut:** _Y’know, sometimes I wonder why I put up with you._

You held your hand to your heart in mock offence, even though the hunter across the screen couldn’t see you, before bringing your hands back to the keyboard to type a quick reply. 

> **CherryPie:** _Hey! Rude!_

> **JustTryingItOut:** _Then I remember you put up with me… So I guess that kinda makes us even?_

> **CherryPie:** _Not by a mile dude…_

> **JustTryingItOut:** _Awh, you know you love me._

Ok, so you were probably a little drunk. But you hadn’t realised how drunk until a second after your fingers had typed a reply that you had promised yourself never to write, even after evenings and night of harmless flirting and jokes. No, you were a big girl, and you’d decided early on to protect your heart by not saying, or writing anything stupid. If for nothing else, just so that you could avoid the tacky band-aids that came with hurt egos and painful rejections. Still, there they were. Words, written by you in a moment of complete drunk idiocy. It was almost as if you had been momentarily possessed. The four black words on the white background of the IM window quickly sobering up your drunk ass. Words written even though you knew J.T, like you, had someone else in his heart.

> **CherryPie:** _Yeah, I kinda do…_

Fuck, you were definitely gonna regret that one in the morning. Damn it, you didn’t always need alcohol to make bad decisions. But it clearly helped move things along toward the eventual fiery explosion of idiocy that was your life. Clearly you should never be allowed to operate either heavy machinery nor any device connected to the internet. Ever. Still, you let your fingers fly over the keyboard in an attempt to erase your mistake, or possibly make it worse. But before you could post your rambled attempt at correcting your drunken words, J.T beat you to it. 

> **JustTryingItOut:** _Really?_

Looking at J.T’s one word question you erased your rambled explanation and did the one thing you could do. You were, after all, a kick ass, amazing hunter who’d faced down demons, angels and killer toys (don’t ask). You knew how to act in situations that needed split-second decisions. Decisions, good and bad, didn’t make ‘em self after all. Not when you were facing down a monster, and definitely not when you had an awkward question you needed to answer. 

Hitting the backspace until your rambled explanation was completely gone you took a second to look at the little IM window and re-read the last few sentences shared between J.T and yourself. Taking a deep breath before finally letting your shaking fingers return to the laptop keyboard.

With another trembling breath you closed your eyes momentarily to remind yourself of your status as badass huntress extraordinaire before you looked at the screen and promptly, without hesitation, logged out. Hell, you were a hunter, not a masochist. Ok… So you were a coward, but a drunk coward. And not too prideful when drunk to run away from your problems.

Damn it, you were so going to regret the whole damned mess the next morning. 

You were thoroughly screwed, and not the good way.


	3. Chapter 3

The next morning was just as bad as drunk you had prophesied, though that hadn’t been a far-fetched guess considering how you made a complete fool out of yourself just hours earlier. You stayed in bed with your eyes closed after waking up to the sobering realization that you had completely fucked up, and that blaming it all on the whiskey would not do you any good. Shit! Drinking and technology never mixed well. Like vodka and beer.

In your own defence, you’d been left unsupervised, drunk, and with a working WiFi connection. That alone spelled doom. _Damn it_ , you weren’t fooling anyone, and least of all yourself. You should know yourself well enough to disconnect everything when you’d been drinking or were planning on drinking. You weren’t some greenhorn when it came to drunken mistakes and sober regrets, you’d had enough of them throughout the years to basically be a black belt in the sacred art of making a fucking fool out of yourself.

Drunk (Y/N) was like the hunter-edition of Jackass. If you knew not to do something, drunk you would do it three times over and scrapbook that shit, adding little inspirational quotes and photographic evidence of every step of the damned train wreck for sober (Y/N) to relive the memories of the disaster on a weekly… Nay, daily basis. No, there was no defending what you’d done… Drunk you was a sadistic bitch, which was something you should have learned years ago.

Yeah, you were fucked. The only thing you could possibly do was to never go online again. Ever. Not even for YouTube or Netflix. Just like how you stopped going to your favourite hole in the wall bar after an evening of tequila shots, 80s karaoke, and regrets. Swallowing you tried to rid yourself of your cotton mouth as your mind flashed back to your words the night before and your subsequent cowardly actions. Your mouth tasted like beer, whiskey and idiotic, drunken, mistakes. Shit, that was it… Your time spent with J.T online, not-so-innocently flirting was over for good.

That was the somewhat good thing about the internet… It made running away with your tail between your legs really easy. Even if your future evenings without talking to J.T would be miserable.

“Fuck!” Your voice was coarse and low in the darkened bedroom. You hadn’t even meant to swear out loud, but hell, yesterday deserved a few good profanities. Your head was pounding and you knew the moment you sat up everything would get so much worse. Getting out of bed wouldn’t just mean dealing with the hangover, but it would also mean facing the world and pretending to the two men in the bunker that you hadn’t made the biggest fool possible of yourself the night before. Because, of course they couldn’t know.. They weren’t even supposed to know you used the webpage. Yeah, you were truly and thoroughly screwed. No hair of the dog or one of Sammy’s disgusting, yet miraculous, hangover smoothies would cure that. 

Only allowing yourself to feel sorry for your stupid drunken ass for another few seconds you finally opened your eyes and turned your head slightly to the side. Wincing as your brain rattled in your skull from the small movement you shot a stern glare at your laptop. Yet, knowing you probably looked like you felt, the glare you threw in the direction of your innocent laptop probably wouldn’t have scared a puppy. Your messy hair and red eyes would probably do the job though. Maybe you should try hunting hungover once, scare them baddies straight with your crowsnest hair and whiskey stained breath.

Damn it, you couldn’t just lie in your bed feeling sorry for yourself all day. No, you needed to get out of bed and actually get something done whilst feeling sorry for yourself. Like a goddamn adult. First on the agenda, a shower. Hopefully a long and scaldingly hot one if Dean and Sammy hadn’t beat you to it. Second, coffee.. Like, bucket loads of coffee. If you played your cards right all that caffeine would hopefully decide to use its powers for good and get you through the day without further embarrassing yourself. Actually, coffee first, second and third, then shower, then possibly more coffee. You needed the energy to even get yourself into the shower. Yeah, this day was gonna be _fan-fucking-tastic._

—

Unfortunately your day of setting the world record in coffee consumption and ransacking the Men of Letters library for a way to turn back time or erase someone’s memories over the internet didn’t go exactly as planned. Your plans had, as they often did in your life, gone straight out the window as you padded barefoot back into the library whilst drying your hair and constantly trying to keep the rain cloud above your hair from kicking it up a notch to full storm warning mode.

You’d barely stepped foot back into the library with no more than three cups of coffee and what was a poor excuse for a lukewarm shower in your arsenal when Sammy had turned to face you. It was all so stereotypically your dumb luck that you found yourself wondering where the damned studio audience that was supposed to laugh at your misfortune was hiding.

And of course dear ol’ Sammy, the damned bastard, looked no worse for wear after yesterday’s drinks. You were sure he’d already gone for a run, had his five-a-day in a smoothie, written a fucking essay on how amazing he was and saved a puppy from a burning building before the sun even rose above the horizon. Ok, so maybe you were a tiny bit bitter at your best friend for his inability to ever get hungover.

Still, no matter how much you felt like the dirt on the bottom of a well-worn boot, Sam’s words easily got you moving. His serious eyes and lack of usual morning greeting clearly underlining the seriousness of his words as he turned away from Dean to face you as soon as you walked through the door.

“Bobby called. It’s demons, we need to hit the road straight away,” Sam barely looked your way before he continued pushing a change of clothes into his worn overnight bag. His hard look and squared jaw paired with Dean’s own solemn eyes was enough to get you moving as you shook off the rest of your hangover and postponed your plans of feeling sorry for yourself. Hunts always came first, you’d kick some ass, _then_ you could wallow in self pity. Never the other way around.

Racing back to your room you quickly packed a few clothes and some of your usual trusty travel items. The thought of a hunt was more than enough to push away all symptoms of a hangover and you moved quicker than you had all morning. That, and the research and subsequent ganking of baddies that a hunt normally entailed helped you keep your mind off of yesterday’s mistake. Demons were bad, sure, but maybe this was somehow also a good thing. The hunt could keep your mind off of your stupid mistakes and function as a more or less clean break from J.T and the page. You could clear your head and effectively run away from the whole hot mess at the same time. Two birds, one very cowardly stone… Just how you liked it.

You normally didn’t contact him whilst on hunt anyway. You had too much to do and focus on during hunts. That, and Sammy and Dean were always around. So maybe you could use the hunt as an excuse to never talk to your internet stranger again, and not feel as cowardly as you currently were feeling about it if you ganked yourself some baddies in the meantime. Ah yes, there was nothing like the blood of your enemies to make you feel like your true badass self again.

Hesitating, you picked up your jacket and looked over at your bedside table where your laptop was sitting, rejected and lonely. Even though you didn’t really talk to J.T when on the road, you normally brought your laptop for research purposes, but maybe you’d be better off leaving it behind. Yeah, this was definitely all for the best. Turning your back to your room you raced back out, ready to go kick some demon ass. Leaving your laptop, and only way of reaching J.T, behind, abandoned in your bedroom.

—

The hunt itself hadn’t been all that hard. Find baddies, catch baddies, kill baddies, have a beer, back home within five days. A pretty routine demon hunt filled with the usual snarky overused lines about heaven, hell, and how exactly those demons believed they were strong enough to actually do more than slightly annoy you and the two other hunters. The rest of your impromptu road trip with a body count however… Not so much.

The mood in the Impala on the way to the hunt had been alright. Tense, due to the case Bobby had given you, but more or less alright. The three of you shared info about the case as the scenery stayed more or less unchanging in the background on the highway. It wasn’t until that first evening that the mood had turned… Not exactly sour, more just apathetic. You’d arrived late at the motel and Dean hadn’t suggested for the three of you to grab a bite or a beer before hitting the sack like he normally did. Which could have been explained by the big guy being tired from the drive of course, but no… He just seemed, preoccupied.

No, instead he’d wordlessly dropped down on one of the two beds in the motel room, claiming it as his before opening his laptop to continue his research in solemn silence. That, paired with your own inability to fully let go of your own slightly sour mood, the motel room had felt more like a not-so-pleasant stay at a state penitentiary than a small town motel/bed and breakfast. Poor, sweet Sammy had tried to lighten the mood, but nothing had really seemed to work.

The damned awful mood had continued throughout the whole hunt. Only slightly lifting during the actual killing of demons part and for the one or two beers after. But it had been _heavier_ even then. Even as you finally returned back to the bunker and entered the library in a single file the mood didn’t seem to improve.

You’d almost had enough of the whole damned thing. Not only had you, willingly and cowardly, given up on talking to the one person you would normally, lately at least, confess those feelings to, but Dean was acting like a complete stranger. It was just all too much to deal with. Honestly you were just one more stupid embarrassment or broken heart away from actually going batshit crazy.

Damn it. Everything (and everyone) you liked was either illegal, unhealthy, unobtainable due to your own damned mistakes, or treating you like air. Dean had barely looked up from his own computer or strung together more than two words at a time during the whole damned hunt. Something was clearly bothering him, and except for the few small smiles he’d thrown in your direction, he didn’t seem to want to share whatever it was. Though you’d willingly take a share of that burden if it was for him. Though you couldn’t tell him that, for… Well, obvious reasons. Like your promise to your own fragile heart of not willingly breaking it by confessing to the hunter.

One good thing came out of the very uncomfortable silence in the car ride back to the bunker though. You’d had the chance to have a good long discussion with the angel and devil on your shoulders about your current placement right between the Dean shaped rock and Chris Gyllenhall shaped hard place. Which, if put into a completely different context wouldn’t have been a bad place to be at all. But in your current situation it really was.

Over the last few days of the hunt, with Dean unresponsive and Sammy focused on other things, you’d found yourself not just regretting your actions, but truthfully really missing J.T. As time went by and you only managed to tease a few words out of Dean you just… You could really use a friend, yet you’d freaking cut all contact with J.T because you were a damned coward. The one person you’d normally vent to when you couldn’t vent to Sammy. Which, in this case you couldn’t, ‘cause A: Dean was his brother, and B: he could never, _ever_ , know you were using the page he recommended. He would’ve kept that one hanging over your head for _years_ if he found out.

So, no… Somewhere between the actual killing of actual demons, the hellish car ride back to the bunker and your not so grand entrance into the library, you’d made up your mind. No matter how it would make you cringe and want to actually dig your way down to hell to hang and chill with Crowley and his hellhounds instead, you’d have to face the music. You needed to clear the air with J.T, or at least the airwaves, or WiFi connection. Or… Hell, Sammy was the one who understood all that techie stuff, you just used it and had him fix it if it broke.

What you needed to do, and do as soon as possible before you chickened out again, was to go online. Between Dean kinda, sorta ignoring everyone during the last hunt and you totally ignoring the full extent of the internet and your poor laptop, you were likely to go insane. And if you were heading that way anyway… Hell, you might as well enjoy the ride and go on a destructive rampage of your own sanity. Starting with logging back into your account after almost a full five days of radio silence.

—

If a part of you had hoped that J.T wouldn’t be online that hope was quickly crushed into a finer powder than the goofer dust in your arsenal. You’d barely booted up your laptop and logged in with shaking fingers before your IM window signalled a new message. It was almost as if he’d been waiting for you, and hell, you weren’t sure you were ready for that.

You’d planned on taking some baby steps out of your cowardly internet free cocoon. Maybe read up about some decapitation methods, or how to make your witch killing bullets even more effective. Y’know? Some light reading to ease you into the conversation you didn’t even know if you wanted to have.

But, J.T was there. His message for once not bringing an easy smile to your lips as your stomach constricted around the massive rock that had been resting in it since what you now fondly thought of as “the incident”, slowly pulling you deeper down into your own personal hell of “Oh God I’m an idiot”.

> **JustTryingItOut:** _Hi! I haven’t seen you online for a few days? I mean… I was on the road, but I looked for you online once or twice during._

Ok… It wasn’t too bad… He hadn’t gone off on you from the minute you entered the page. No interrogation… _Yet._

> **CherryPie:** _Yeah, it’s been a bad couple of days I guess._

> **JustTryingItOut:** _Shit… You ok?_

> **CherryPie:** _I guess… I mean, nothing’s on fire, I didn’t end up going to jail and nobody died. So it could’ve been worse…_

> **CherryPie:** _Or better… Depending on how you view jail time and body counts. Which honestly could go either way for me depending on the day._

Aaaand… There it was. Your famous armour made from scraps of sarcasm and poorly veiled jokes and padded with sass and diversions to keep others from turning conversations, and feelings, around on you. That wasn’t exactly why you’d toughened up enough to re-enter the page. You needed to clear up the mess you made.

You were a big girl. Big enough to admit you might, possibly, ok definitely like two men. Though of course that was debatable, ‘cause it was a hell of a lot easier to do so online that to the hunter in the library. And even then you doubted you were big enough to fully deal with it past typing some more or less anonymous words in a chat window online.

> **CherryPie:** _It’s just been… Rough._

Ah yes. You were the goddamn goddess of clarity. The ruler of the land of “let me spell it out for ya". Truly, there was no braver cookie in the land than you, (Y/N) (Y/L/N). All praise to you, the biggest, bravest coward of them all. The lion from the Wizard of Oz was probably seething in jealousy right about then. Rough? _Fucking rough?_ Yeah, that explained it all doesn’t it? Yet, J.T didn’t miss a beat before responding to your vague answer. 

> **JustTryingItOut:** _Damn. That doesn’t sound good. Him?_

Ok, this was it. The moment of truth. Fuck. Once, you’d fought a druid witch that set a bear after you and you’d freaking rodeoed the shit out of that situation. That had been scary. This… This was _terrifying_. Time to be your badass self and tell him everything.

> **CherryPie:** _Him, yeah. And, I guess kinda you?_

Ok, so you clearly needed some lessons in both bravery, clarity and sharing your emotions. Damn it, you’d seen fog clearer than you were being. Luckily however, J.T seemed to understand what you were hinting at without any further input from you. Which was probably for the best since you were a step away from pulling out that old pictionary set Sammy brought back one night to try and show him in images and hand gestures. Which of course would have failed miserably. Since… Well, J.T couldn’t actually _see_ you. 

> **JustTryingItOut:** _Ah… I thought maybe you didn’t want to bring that up. Considering you kinda left me high and dry with unanswered questions last time we spoke. Though honestly, I was hoping you would…_

> **JustTryingItOut:** _Want to talk about it I mean, not leave me high and dry._

> **CherryPie:** _I’m sorry.. I know it’s no excuse but I wasn’t exactly sober…_

> **CherryPie:** _Would you believe me if I said my laptop was drunk? Or maybe possessed?_

> **JustTryingItOut:** _Considering you already admitted to being the drunk one? No, unfortunately not._

> **CherryPie:** _Damn it, should’ve seen that one coming._

> **JustTryingItOut:** _So… If you were just drunk. Does that mean you didn’t actually mean what you said?_

And there it was, the question that last time had you running for the hills, not caring if they were the type with musicals and massive talented families or the type with eyes and mutants. This time however you went against your own nature and honestly answered your internet stranger. Hoping your honesty wouldn’t mean the end of your online friendship or the start of a broken heart. 

> **CherryPie:** _No…_

> **CherryPIe:** _I mean, I meant it. I’ve kinda come to like you. I know it’s not right, and I still love him. But, yeah… There ya go. The more you know and all that jazz._

> **JustTryingItOut:** _Oh thank God._

> **CherryPie:** _?_

So, that wasn’t the answer you’d thought you’d get. Though of course he could just be relieved you weren’t forcing him to actually respond to your mixed emotions and clearly greedy heart. Still, to satisfy your curiosity you still hadn’t been able to keep yourself from sending the little non-committal question mark. Allowing him to choose what question to answer, and how. Hell you’d accept the dictionary explanation of who God was if that’s how he wanted to play it.

> **JustTryingItOut:** _I was hoping you’d say that. ‘Cause, honestly? I’ve been feelin’ the same way. I know it’s not right, I still love her, and this whole thing is damned confusing. But… Yeah, I like you._

At what age was it no longer considered ok to dance around your room like some teenage girl in a rom-com who just got asked out to prom by her crush? You didn’t know, and honestly, you didn’t really care. Yeah, you were realistic enough to know nothing would ever come from the whole thing. But… It felt good to be liked. It felt good to have something not be one-sided for once.

> **JustTryingItOut:** _So, what now?_

J.T’s question came after a lengthy silence from your side as you multi-tasked by wrestling the butterflies in your stomach back under control whilst debating internet protocol when it came to online confessions. Clearly, J.T didn’t have the answer to the latter of your two current activities either if his message was anything to go by.

> **CherryPie:** _Now… Now I guess we just go back to chatting? Y’know, just… Talk like normal? I mean, there’s not much we can do. Considering we only know each other on here. And considering, her and him._

> **JustTryingItOut:** _Yeah, you’re right. That works for me._

> **JustTryingItOut:** _So… That takes care of us. Of you and me I mean… Not that we’re an us, but yeah… What about him? Y’said he was also part of the, doom n’ gloom in your life right now._

> **CherryPie:** _I didn’t really phrase it like that, but yeah… Still. Maybe it’s better if we don’t, y’know, talk about him? Since…_

> **JustTryingItOut:** _Hey! I’m here for ya. I know full well that it’ll suck to hear you talk about him, just like it probably sucks for you when I talk about her. But, I like it when you listen, or read I guess… And I wanna do the same for you._

You frowned at the screen, fingers hovering over the keyboard. It felt wrong, to confess something so precious, and then turn around and complain about another man. Yet, at the same time you did feel the same way as J.T. Even though you liked your internet stranger and he liked you, you were too far apart. Just, being there for each other and dealing with the two other loves in your equally greedy hearts was all you could do.

> **JustTryingItOut:** _If it’s too hard for you I understand. I’m not sayin’ I won’t feel kinda jealous, but I really wanna know how you’re feelin’._

J.T’s words showed up on the screen before you could decide on the right thing to say, his words making the decision for you. You really did want to confide in him. Sure, you loved your little funny moments and IM based flirts, but talking to him always helped to raise your mood. 

Even when you were discussing the harder things. Which was probably because he let you vent, then moved on. You didn’t feel the need to dwell on things with him. And somehow J.T always seemed to make it seem easy for you to talk about everything and anything. 

Finally letting your fingertips rest gingerly against the keys you wrote out a hesitant message. It felt weird, sure, but after all losing this…. The talks and the free counseling, was part of what had made the distance you put between yourself and J.T so much harder.

> **CherryPie:** _He’s been… Distant. More than usual at least. Constantly locking himself up in his room or avoiding talking to me by focusing on research or whatever. It’s hard… And I guess, missing you made it harder._

> **JustTryingItOut:** _Honestly, I haven’t been the easiest to deal with since that night either really. And I think she noticed. I just… I love her, I really do, but… There’s you too._

You sighed and let your head hit the wall behind the bed, staring at the screen with a look of frustration so concentrated that you could’ve bottled it, watered it down, and sold it for a nice profit. 

> **CherryPie:** _Yeah, damn it’s just all so confusing. Maybe we should just, talk about something else that him and her? I need to smile right now, not scowl at the screen._

> **JustTryingItOut:** _Awh, not feeling great are ya? Don’t worry, good ol’ J.T is here to make you feel better._

> **CherryPie:** _Shut up you major dork._

His words still teased a smile out of you, even though you couldn’t help but to read his words in Dean’s teasing tone. The tone the older hunter would use on you whenever you got slightly annoyed at some bastard in a bar or on the road. One of the trademark Dean ways of making you laugh. A role that now had fallen onto your internet stranger whenever Dean was the one who made you, well… Not frustrated, just… Ok, frustrated. Totally and utterly frustrated and about to go completely insane.

> **JustTryingItOut:** _Chin up princess. Your crown is slipping._

Raising an eyebrow, you gave the screen your best impression of one of Sam’s bitchiest of bitch stares with a small smile ruining the overall aesthetic of the look. So, that was the way he wanted to play it? Ok, you were game. Anything to stop you from moping around feeling sorry for yourself.

> **CherryPie:** _First if all, cheesy line J.T. And, princess? Dude, you know I’m a goddamn Queen._

> **JustTryingItOut:** _Hah! Yeah yeah. Keep telling yourself that Cherry._

Though you knew your internet stranger, the same man who still looked like a celebrity mix in your head and who’d just confessed to feelings you both shared, couldn’t see or hear you. You still let out a little sound of mock offence and teasingly glared at the letters. Clearly leaving enough time for him to sprinkle a little flirt on top of his own words, taking most of the teasing out of ‘em and easily making you smile.

> **JustTryingItOut:** _So… If you’re a queen, that means you need a king right? Or at least a knight in some nice, shiny jeans?_

> **CherryPie:** _Hmmm.. Firstly, I said goddamn Queen with a capital Q, meaning I kick ass instead of just being royal and shit… Secondly, I wouldn’t say need. I know my history J.T. Historically there’s been plenty of strong queens without kings._

> **CherryPie:** _But… If it’s you I’ll consider it._

> **JustTryingItOut:** _You really know how to sweep a man off of his feet sweetheart._

—

Things went back to normal after that. Or at least as normal as they got in your messed up world. Your mutual confession to your internet stranger didn’t stop your easy nightly chats, though J.T _had_ taken to upping the flirt a bit certain evenings. The only real change in your chats were that they flowed easier after your shared feelings. It had somehow made it easier to let him in on the inner workings of your fucked up mind.

Everything just somehow flipped that evening, and just seemed _better_. Even Dean, though still sometimes slightly lost in his own cryptic thoughts, seemed to have gotten out of the funk he’d been in. Sure, maybe you’d just actually lost your mind and everything wasn’t all roses and rainbows or beers and burritos, but things finally seemed to be working themselves out.

Ok, so you’d basically, effectively chosen the blue pill and to stay in the matrix. You knew your heart couldn’t take the split feelings for long. But damn, taking the red pill was easier said than done. Especially when the matrix had all the conveniences you could need, and a man who seemed to like you back for once. Basically, if you were to be honest with yourself, which most of the time you couldn’t really be bothered to be, your current equilibrium couldn’t last forever.

You needed to draw a line, or at least make some choices. Because even though you now knew you both felt the same conflicted feelings, the guilt over liking two people didn’t get any easier to bear. And knowing that J.T could be suffering through the same thing. That just made it a hundred times worse. You’d always had a bit of a bleeding heart when it came to others more than yourself in that way.

Still, every time you went online, determined to talk to J.T about it, you failed and your conversations kept going about other, more innocent, or not-so-innocent things instead. Just like it had done that evening as well. You’d tried, but, well… There were just more pleasant things to talk about. Like… Absolutely anything else because you sucked at confrontations. At least those that didn’t require a weapon of some sort.

You’d been talking for hours, like normal, and the conversation was no closer to the subject you’d promised yourself to bring up. And honestly you didn’t believe it ever would be. You’d even come equipped for the all-night type conversation you normally had with J.T. Sneaking a few beers and an extra big slice of your favourite cake into the bunker and your room right after Dean and Sam both left for bed.

Your talks with J.T could last for hours. Your blood sugar levels, not so much. You needed snacks if you were gonna have another all-nighter. Ok, so maybe you hadn’t really been serious about having an actual confrontation and sorting your shit out. Talking to J.T was just… As close as you thought you’d ever come to heavenly bliss for your mind, at least when the unnecessary guilty feelings took a backseat and let you enjoy the ride.

And even with your repeated promise to yourself to sort your shit out, most of your conversations were still less red pill, blue pill and more just… Like that evening’s one. Simple, fun and full of quick back and forth quips.

> **JustTryingItOut:** _Do you ever sleep? Or do you even need sleep?_

> **CherryPie:** _Sometimes I catch myself pondering that question… It keeps me up at night._

> **JustTryingItOut:** _Cherry, ladies and gentlemen, always the comedian._

> **CherryPie:** _You’re no better though, you’re always online too!_

> **JustTryingItOut:** _That’s just ‘cause I’ll know you’ll be here._

You grinned at the screen, lifting your bottle to the screen as if you were toasting the smooth motherfucker, before bringing it to your lips for a sip. Putting the bottle back down you didn’t let it slip that you liked his response though, not when there was more teasing to be dealt out left in the bag.

> **CherryPie:** _Yeah, keep tellin’ yourself that big guy._

> **JustTryingItOut:** _Alright, so we’re both chat addicts, we should start a group. Meet up once a week to discuss over awful coffee and dry cookies._

You laughed at the image J.T painted in your minds-eye before taking a quick bite of cake, letting a satisfied hum out along with the empty desert spoon. That shit was gastronomically orgasmic. You’d never be able to eat a slice of that cake out among people, not when every bit you took sounded like the backtrack to a 70s porno.

> **JustTryingItOut:** _So what are you actually up to? Other than talking to me? ‘Cause you’re taking forever to answer._

Looking back down at the screen you grinned at J.T’s latest message. Clearly he got sick of waiting for an answer to his latest quip as you’d chosen cake over comeback. Reluctantly you let go of your spoon and typed your honest reply to his question with a smile. 

> **CherryPie:** _Eating cake, because why the fuck not. Some girls flee balls and lose shoes at midnight, I crave sugar._

> **JustTryingItOut:** _Yeah right…_

> **CherryPie:** _I also have beer. Need to stock up before our chats y’know._

J.T didn’t seem to believe you, and once more you caught yourself making faces at your computer screen though he couldn’t see you. The hand not resting on the keyboard reaching for your half drunk bottle of beer, and shaking it in front of your screen before taking a sip. Because, hell, you’d already committed to the whole thinking he could see you through your screen thing, so you had to see it through till the very end. Your mom didn’t raise a quitter.

> **JustTryingIitOut:** _Seriously, cake? Really? I have so many questions…_

> **CherryPie:** _Hey, don’t judge me. We talk for hours normally… I get peckish. Plus, it’s my favourite cake and if I tried being an adult about it and eating it in the kitchen like a normal person he would’ve most likely stolen half. Had to smuggle it into my room like a damned shady drug lord to eat it in peace._

No need to mention the porn-like sounds eating the damned cake made you make… That might be too much for poor J.T to handle.

> **JustTryingItOut:** _Alright, no more talk of cake. Now I just wish I had cake too._

> **JustTryingItOut:** _I wish you could share your cake with me…_

> **CherryPie:** _Hell no, there’s no we or us in cake. This bad boy is all mine._

> **JustTryingItOut:** _You wound me Cherry. Seriously, ouch…_

Suppressing a tiny evil laugh you took an extra big bite of cake before writing back. Once more procrastinating on the more serious conversation you knew you’d have to have at some point… Right then you just wanted to enjoy two of your favourite things in the world. And not worry about what was lying in wait outside of your safe little corner of the matrix.


	4. Chapter 4

The anonymity of the computer screen had made it too easy for you to open up more than you’d ever meant to open up to anyone. Especially considering you were still fighting your whole red pill, blue pill battle. 

You, unfortunately, came to this realisation quite late. Almost a full month after your first drunken confession to the internet stranger. By the time you realised you had already spent countless evenings, nights and the occasional lazy afternoon talking to J.T about all the little things that occupied your mind. Including your messed up emotional state. 

Specifically your conflicting feelings for the two separate hunters.

Yeah, so maybe it was stupid to talk to one of the two men you found yourself attracted to about said attraction. Actually it was _abso-fuckin-lutely_ the stupidest, most insane thing you’d done, and you’d done some fucked up shit. 

Still, J.T wanted you to share and he had only responded in kind. And since that vulnerable moment where you had confessed your confused state of mind and him his, your evenings had often returned to the topic as you both felt so close to each other, yet still in love with your respective hunting partners. 

Your conversations easily ranging from light and easy to what read like a bunch of really _really_ sad one-line love letters.

And every time you spoke you found another reason for not ending it. Whether it was the easy, friendly chats that read like the script of some low-budget sitcom or the more in depth chats where everything he said made it seem like J.T was reading your mind. Or like he had just bypassed your mind completely and hooked an amplifier and full surround sound system directly into your heart. 

Those nights were always the sweetest, yet the most bitter and hardest to deal with. Like whiskey and dark chocolate.

> **JustTryingItOut:** _Sometimes I just wish you were here, maybe I wouldn’t be feeling like this then._

> **CherryPie:** _I know what you mean. Things are… Fucked up atm._

> **JustTryingItOut:** _ATM? I thought you said you were in bed?_

You choked back a small laugh at the other hunters lack of “internet speak” knowing full well how much he hated it the few times you fell back on your lazy typing and used abbreviations instead of full words. 

Though you’d caught him using them for hunter terms more than once.

> **CherryPie:** _At the moment._

> **JustTryingItOut:** _Ah! Then say that, I was thinking you were at an actual ATM or something. I hate those damned text words. Geez… Ruining the mood like that._

> **CherryPie:** _Awh, the poor old man can’t deal with some abbreviations. Sorry Romeo!_

> **JustTryingItOut:** _I’m not that old! And… Shut up, but really… Why are you wherever you are, and not here?_

> **CherryPie:** _‘Cause life’s fucked up and unfair, that’s why._

> **JustTryingItOut:** _Real life is messy as a hunter, but this ain’t much better._

The muted little laugh that left you was possibly a little more negative that it usually was, but fuck it. You were having one of your heart to heart Oprah moments. 

You were allowed a bit of wallowing in selfish self pity. Or more like going fucking skinny dipping in it. In cement block shoes, while holding a plugged in toaster, during a damned snow storm. Because that was pretty much your idea of fun lately.

> **CherryPie:** _Tell me about it.. It’s all a mess, I’m a mess._

> **CherryPie:** _But hey! Look at the bright side! I might be a mess, but at least I’m a fucking hot mess…_

> **JustTryingItOut:** _Not sure that means what you think it does sweetheart._

> **CherryPie:** _It sure as hell does now._

> **JustTryingItOut:** _Ok, wait right here. I’ll inform the masses._

Your next smile came a little easier as you stared fondly at your computer screen the same way that some might smile at a nostalgic family photo. How was there even room in your heart to fit everything you felt for both Dean and your internet stranger? 

You didn’t know. But you feared one day your heart would attempt a jailbreak out of the cage that were your ribs and this whole mess would blow up in your face.

Yet, as you congratulated J.T on his very inventive plan for spreading your reinvented meaning of the phrase ‘hot mess’ (which included somehow taking over several well known web pages by “McGyvering that shit” since neither of you knew hacking) you pushed those thoughts aside. 

Crossing your fingers, mentally of course since your fingers were busy tapping away at the keyboard, you took a deep breath and hoped that you still had time before everything came crashing down around you.

—

So, this have courage, hear me roar shit was easier said than done. Especially when it came to making hard decisions. 

Bad ones… _Hell,_ that shit was easy. Hard ones, not so much. You _knew_ you had to sort your stuff out. To either try to let go of Dean in your heart and mind, or to go back to the more or less platonic no-flirting chats with J.T. 

This was your stereotypical “can’t have your cake and eat it to”-moment and unless you got your shit together you knew you would regret it. And not in that cakeless, stomach pains from eating too much way. No, it would be heartache, and that shit was a thousand times worse.

You’d even succumbed to movie stereotypes in your quest for the holy grail of getting-your-shit-together by giving yourself honest to God movie mirror pep-talks. 

Every time you were in the shower you’d tell the slightly damp (Y/N) in the mirror to stop or to move on or to do _something_ before your own damned internal guilt trip sent you on a one-way trip to the closest padded room without a ticket or gas money. You were basically moments away from “Go directly to the nearest psychiatrist, do not pass go, do not collect $200”, and it _sucked._

You’d just stand there, in your stupidly small towel, telling yourself to be a freaking hunter. To use the strength that had to be hidden somewhere inside of you to sort shit out like a grown-up instead of building structurally fragile pillow forts around yourself. To deal with this like you dealt with everything else, ‘cause that’s what you did… 

You _dealt_ with bullshit on an almost daily basis, you didn’t just put it on a plate and call it a brownie. Yet, even your own reflection didn’t seem to believe you as it stared back at you after every shower. If anything it just looked to believe you less and less with every stupid “pep-talk”.

Also, you were pretty sure Sammy had overheard one or two of your more vocal fights with the weakling in the mirror. At least it seemed that way, based on the semi-curious looks he’d been throwing your way lately. So not only were you dealing with a situation that might permanently damage your already fragile heart, but your best friend was starting to think you were losing your mind. Which, honestly, you were surprised he hadn’t started believing earlier.

Luckily though, you’d been cautious enough even in your “Pulp Fiction” imitation moments to stay as vague as possible when talkin’ to yourself. So the big guy should, hopefully, still not know what the whole mess was about.

So, between your own restless mind and recreating scenes from famous and not-so-famous movies alike you’d been spending your days, outside of chatting to J.T or hunting and movie nights with Dean, continuously cycling through the five stages of acceptance. 

_Fuck_ , you’d probably gone through them all about 50 times before every new chat and every new moment shared with Dean. Actually, you were pretty sure you’d even managed to create a few new stages. Shame wasn’t one of the original five, was it?

That evening was no better… 

You’d spent most of the afternoon and lazy non-hunt evening relaxing in the library with the Winchesters. Pretending you weren’t insane and trying to decide if you needed a bottle of whiskey, a gallon of coffee or just to start a new bad habit to fully start fucking up your life. 

Still, as Dean excused himself to go check on his arsenal, you’d been unable to actually make a choice. Other than shortly after, retreating to your own room and booting up your ancient laptop.

Shit, you knew you should be thinking about fixing the whole mess, but like every evening before it, all you wanted to do was to laugh with J.T and talk about something stupidly unimportant again. 

When did “old enough to know better” actually start kicking in? ‘Cause you sure as hell weren’t getting any younger, and you damned sure wasn’t smart enough to not make a mess of things, nor clean up the messes you’d made, yet.

Logging in you were happy to see J.T was online, easily pushing away your conflicting thoughts as you sank back down into the mattress and pulled your laptop into your lap with an easy smile.

> **JustTryingItOut:** _Took ya long enough…_

> **CherryPie:** _Honey, I’m worth the wait._

—

A few nights later you caught yourself sighing as you stared at the screen. 

Your chat had gone the more dramatic route again that evening and your heart felt, conflicted, to say the least. Lately you’d barely seen Dean, unless you were sparring together in the afternoon, watching a movie, or on a hunt together. Still, you couldn’t deny the attraction you always felt towards the man whenever he was near. 

Yet, then there was these moments. Just talking to J.T… And both types of interactions left you breathless with a swarm of giant mutant butterflies in your stomach and a severe case of vertigo as your heart flip-flopped between the two hunters in your life. And even after a month, you couldn’t seem to get it together.

How many times had you yelled at the TV screen at some man or woman who seemed unable to sort their shit out? Told them to just clean up their mess and move on with their lives… 

And yet there you were, a fucking hurricane. The mess you’d made of your heart only getting bigger with every rotation, every beat. And just like you’d yelled at the poor actors and actresses on the TV screen, you wanted to yell at yourself now. Sort things, clean up the mess, _make up your goddamn mind_!

You felt selfish, and conflicted. 

You’d sworn up and down for years that only Dean could make you feel, _love_ , the way you did. Which was why you’d been unable to let go of your feelings for the hunter even though you knew you should. Yet there you were… 

Somehow attracted to a complete stranger and constantly wishing the two were the same person or that you at least could somehow let go of one of them.

The constant what ifs had started playing a big role in your daydreams. What if Dean was down the hall talking to you? What if he loved you back and the two hunters were the same person? What if you went and met J.T and he was actually Dean, or, the more likely scenario, a total asshole? What if you met him and he was some other hunter you knew? What if… By some weird twist of fate, he wasn’t a hunter at all? 

Or worse yet; what if you met J.T and you still liked him?

Hell, you’d played with the thought of meeting J.T several times over the last month. Or just stopping talking to him all together once more. Just, cut off contact, pretend you fell into some feelings and just brush all that shit off. 

Anything to end the guilt you somehow felt at your own messed up emotions. And though he hadn’t said anything, you were pretty sure J.T suffered through the same thoughts.

Though, if you did decide to go cold turkey, you wouldn’t just run away again. Just like you had confessed a lot of stuff over the last month to J.T, he had confided in you too. Specifically about your last battle with cowardice. 

In your world, death could be hiding around any corner, probably munching on some nachos. And when you were gone for five days, J.T had assumed the worst. No, if you were gonna go the cowardly route again, you had to let him know.

You were pulled out of the quickly descending spiral that was your own mind by J.T’s message as the little “unread message” icon showed up on your screen once more that evening. 

Your internet stranger proving yet again that he truly did possess mind reading powers with feelings that mirrored yours.

> **JustTryingItOut:** _Damn it… This is all so confusing… I’m pissed off at him, and I’m equally pissed of at myself._

> **CherryPie:** _I know what you mean… I like you, but I still love him._

> **JustTryingItOut:** _And I love her. Which is why I’m pissed off at myself. I’m here feelin’ jealous of a man I know nothing about, and at the same time loving someone else. It’s not fair to her or to you._

You felt your own jealousy burn in your throat, making you slightly nauseous as you shared every single one of J.T’s mixed emotions. Maybe, just maybe it would be better to just get it over and done with. To just… 

Cut one of the two men out of your life. 

Even if you felt attracted to the image of the internet stranger in your mind, you couldn’t keep going like this. Dean still occupied most of your heart, and just like you knew you’d always love him, you also knew that she’d always stay in J.T’s heart. There was no way the two of you could work out. Not when what you most likely had were just two heartbroken people licking each other’s wounds.

> **CherryPie:** _I feel the same, I just. Fuck it, I mean I feel so guilty. I feel dirty and bad. Love should be simple right? You either love someone or you don’t. And when you love that person, it’s only them. At least that’s what I believed until…_

> **JustTryingItOut:** _Until I started chatting to you._

You felt the by now familiar squeeze of guilt and selfishness on your heart as you looked down at the keyboard of your laptop. Shaking fingers lifting to write a reply you knew you couldn’t take back. 

Yeah, this was bad for both of you. It would be better to stop it. Even if it would hurt for a little while. It was the best choice. Even if just trying to type it out had you shaking. 

Hitting enter you sent your message before you could regret writing it. Seeing the words show up directly under J.T’s. 

> **CherryPie:** _Maybe we should just, y’know, stop?_

> **JustTryingItOut:** _What do you mean?_

> **CherryPie:** _Stop chatting… Look I have a hunt in two days time… I’ll probably be gone for a while since we’re heading out of state. Maybe that’ll be a clean break? I mean… These chats aren’t doing either of us any good._

> **CherryPie:** _We don’t know anything about each other. If we stop using the page then we won’t have any way of contacting each other, and then maybe the guilt and fucked up emotions will stop?_

> **JustTryingItOut:** _Isn’t that just running away though?_

> **JustTryingItOut:** _I hate how I’m feeling, but I’m not gonna deny that I like you. Even if I can’t stop loving her. I know it’s wrong, and I hate that I miss you when I’m out hunting with her, and miss her when I’m talking to you. I can’t stand it, but I couldn’t stand losing you even more._

> **CherryPie:** _It’s not fair. To ourselves or to them. Though he doesn’t love me, I do love him. I love him, and I like you, but I can’t give up on my feelings for him. No more than you can give up on her. We’d just end up hurting each other._

> **JustTryingItOut:** _I know. Hell, I know all of that and I hate that I want you when I should be loving her and only her like, I have been doing for years. I’ve even had the same thought as you about stoppin’ this before, but…_

> **JustTryingItOut:** _Look, I’m heading out for a hunt as well. How about we meet up? Just once, when we’re both on the road. If we don’t feel the same when we meet face to face then I’ll stop using the page completely._

You felt your heart jump into your throat with enough power to actually hurt as you stared at the screen. Stopping the rebuttal you’d been typing when J.T’s second message appeared in the little chat window. 

_Fuck,_ you were freaking out. Not once, in your wildest dreams, ok so maybe in your _wildest_ dreams but definitely not in your normal ones, had you ever thought you would ever actually meet J.T. 

Sure, you’d played with the idea, but mainly in the same way you played with the idea of just randomly kissing Dean one evening to see how he’d react, as in… A completely delusional form of playing that you had never, _ever_ , planned on acting on. 

Still, what had you freaking out the most was the fact that you were actually considering it.

You didn’t actually know the man on the other side of the screen. Hell, you didn’t even know if your hunts would actually be anywhere near each other. Yet, you somehow, if only for a moment, considered what he was offering.

> **CherryPie:** _What?_

You couldn’t make yourself type anything more as you kept staring, dumbfounded, at the screen of your laptop. Re-reading the last few things you’d talked about as you tried to wrap your head around his suggestion. 

You tried to picture the meeting in your mind, unsuccessfully. What, so he’d come along with his stunningly beautiful Scarlett Johansson lookalike of a crush and you’d bring Dean, and then you’d just have the most fucked-up double date in history? 

Four hunters, not meeting to kill monsters, but to kill time? Yeah, no, that sounded like the movie script in the scrap pile of some big shot directors office. 

What would you even say to Dean, the man you actually loved? Oh, by the way, can we just make a quick stop up the road so I can meet the man I’ve been talking to online? It’s no biggie really, I just want to see if he can make me forget about my mind numbing crush on you. 

Yeah, right. That would go down about as well as shards of glass. 

> **JustTryingItOut:** _I know it sounds kinda out there and crazy._

> **CherryPie:** _Sounds crazy?!? It IS crazy!_

> **JustTryingItOut:** _Maybe, but I don’t just wanna stop chatting to you. I don’t think that will fix anything either. I’m not asking you to meet me alone, hell, we could just say we’re meeting another hunting party. Or we could meet somewhere with loads of people?_

> **CherryPie:** _I’m not saying no because of internet safety, I’m pretty sure I could take anyone down if I wanted to, and I wouldn’t be stupid enough to meet someone out in the middle of nowhere. I just don’t think this is a good idea._

> **JustTryingItOut:** _I won’t force it if you don’t want to meet, but I do want to meet you._

> **JustTryingItOut:** _I just don’t want you to disappear on me like that._

You grimaced in pain as you looked at the screen. 

He was leaving it up to you, and you should’ve been happy. But hell, you honestly didn’t know what to feel anymore. You liked someone you had never met and at the same time loved someone you saw everyday. You wanted to cut off all ties with J.T, yet wanted to always keep him close for those little night time conversations. 

Yeah, you were in no state to make any big decisions. 

> **CherryPie:** _Even if I said yes, and I’m not saying yes, how would that even work? The U.S is pretty fucking big. You might be going somewhere completely different from me. Are you saying we both travel hours in the opposite direction of our hunts to meet up? Pretty sure neither of our hunting partners would agree to that._

> **CherryPie:** _I mean, hell I could be goin’ to Alaska for all you know._

> **JustTryingItOut:** _Ok, yeah… I might not have thought it through properly. But if we are going to be in the same area, or at least just a few hours away… Would you at least think about it?_

> **JustTryingItOut:** _I know it’s unfair to you… And to her, but I feel like I need to meet you. I need to figure out if what I’m feeling for you is real, even though I know I’ll keep loving her. It’s fucked up, I know and I’ll understand if you don’t want to meet._

> **CherryPie:** _And how will we even know where to meet up? Or if we’re even in the same area? I’m not sure about this J.T… Maybe it’s better to just leave well enough alone. If we just end this now, I’m sure someday it’ll just be a memory we can look back at fondly._

> **JustTryingItOut:** _I’m not sure… Maybe I’ll look back at it and regret it? I don’t know… And I know what I’m asking is really selfish. But…_

> **JustTryingItOut:** L _ook. I’ll be hunting some werewolves over in St. Louis, Missouri. If, by any chance, you’re near there… I would like to meet you, Cherry. There’s a diner there, by the Mississippi river… I’ll bring my laptop and I’ll go there. Around three days from now. If you’re anywhere nearby and if you feel like meetin’ me, come there._

You lost all ability to actually respond as you looked at the words written on your screen. 

Could it really be a coincidence that you were going to the same city, hunting the same flea-ridden monsters? It couldn’t, _could it_? No, there was no way the universe had somehow produced that kind of miracle. Both of you out to get the collarless mutant cousins of Fido, maybe, but it the same goddamn city? 

No, it _couldn’t_ be a coincidence. 

Resting your fingers on your keyboard, but not typing, you tuned out the rock song playing through your headphones as you made yourself think back on your countless other chats with J.T. Looking for all the little hints, the little coincidences that once added up would only solidify the single answer in your mind. 

The two men you’d come to care for shared a lot of similarities, which you’d always just brushed off. And then there was the fact that your hunts somehow always fell around the same time…

No, it couldn’t all be coincidences. 

Were you sure enough to just run down the hall to confirm it? Oh. _hell_ no. Not when sitting there, wrestling with thoughts of what you should do, you couldn’t completely rule out that you were just making connections where there were none. Selfishly stopping your own guilt by making the man you loved and the man you somewhat liked into the same person, like you had done several times in your delusional daydreams.

Still, there was only one way to know for sure…

> **CherryPie:** _Ok…_

> **JustTryingItOut:** _Ok, you’ll think about it? Or ok, it’s time you stop being an idiot J.T?_

> **CherryPie:** _Ok, I’ll meet you… In Missouri. 4 pm, three days from now. Just.. Send me the name of the diner and I’ll be there._

—


	5. Chapter 5

Saying you spent the next few days in a daze was the biggest understatement this side of eternity. 

You barely even noticed time passing as you switched between regretting your choice and trying to figure out if your hunch was right. Neither of which had made any big impact on your decision nor made you truly certain that things were going to go the way you wanted them to. The only thing it had done was further develop your own personal brand of batshit crazy. _Patent pending_.

Hell, add the fear of a negative reaction into the mix and you were just a big ball of nerves. Which didn’t get any better once you actually scooted into the backseat of the ebony Impala and headed out for the long drive from Lebanon, Kansas to St. Louis, Missouri. 

_Whoop-dee-fuckin-doo_ , a road trip with the man you loved who was possibly also the _other_ man you loved was just what the doctor _hadn’t_ prescribed.

You had over 7 hours where you couldn’t pace around and call yourself an idiot or fantasize about how the meeting would go down. Not really your idea of fun. Anything would be heaven compared to the hellish situation you found yourself in, a fist fight would feel like a day at the spa in comparison. 

Hell, if you made it through the drive there without imploding it would be a miracle. Like, one of those praise the lord and make it a public holiday type of miracles.

Your mind had been a mess of failed attempts and near misses since the meeting was decided. Just a long list of ‘almosts’. 

You’d _almost_ gone online several times in the time between sending your last messages to J.T and actually leaving for the hunt. You’d _almost_ asked Dean straight out if he was J.T. You’d _almost_ faked being sick to get out of the hunt… Hell, you’d _almost_ cancelled the whole damned meeting a thousand times!

Yet, you’d done none of those things, ‘cause lately “procrastinating to not make difficult choices” had become your weirdly long middle name. 

Instead your only actions had consisted of freaking out and stopping yourself just before gathering your courage to ask Dean. Or opening your computer only to _not_ log in to the website that was now a bigger strain on your nerves than anything else had ever been. 

Your childhood action hero figurines would be disappointed in you if they could see what an action-less adult you’d become. You could almost picture your worn out Wonder Woman figure shaking her head at you in disgust from the bookshelf in your childhood home.

Was it possible to go mad from mixed emotions and counting down seconds? Cause if it was you were close to booking a one way ticket with no return policy to the closest asylum. The thought of going there and having him show up to see who “CherryPie” actually was… 

_Damn it._

Hell, maybe he wouldn’t even show… Maybe he suffered through the same thoughts of glee-filled regret you did and backed out last minute. 

_Ah,_ if only he would stand you up and you wouldn’t have to deal with your own damned emotions any more. A girl could always hope… 

He _had_ seemed pretty happy when he sent you the details before you logged off though. So you doubted he would. And J.T, no Dean, _no…_ The J.T that could possibly be Dean, didn’t seem like the type to stand someone up like that. 

_Fuck_ this thing was more messed up that your t-shirt drawer back at the bunker.

Still, if it _was_ Dean… How could he possibly react to learning you were Cherry? Maybe he would be happy? Maybe he’d be pissed off and think you’d been playing with him… Hell, maybe it wouldn’t even be him and your guilt and mixed emotions had actually made you delusional. 

Would that be worse or better? You honestly didn’t know anymore. Though if you really were losing your mind you would’ve appreciated a clearer sign. Like, talking to a cartoon character or maybe seeing fairies or _at least_ a goddamn voice-over narrating your life.

Anything was better that the endless questions that all bowed down to the main honcho of a question. Namely, what the _hell_ would happen when you stepped into that diner? You didn’t know and you doubted the long drive to cross the state-line would magically provide you with any of the answers you needed.

Damn it, you hadn’t been this tightly wound up when facing down fangs, shifters or demons before. The last apocalypse? That shit was chill as fuck next to this. 

Damn it, damn it, _damn it all to hell_. Or no, not hell. Bad things had a tendency of coming back from hell, like demons… Damn it all to purgatory, that place was damned near inescapable. 

Either way, the whole fucked up mess should be damned to _somewhere_. You were either the biggest idiot ever or… Nah… That was the only option.

You hadn’t even told J.T that you were hunting the same thing, in the same _damned_ town. You were too afraid that he, like you, would put two and two together and find that it couldn’t be a coincidence. Unless you were delusional and it was all a coincidence… But if it wasn’t… 

_Fuck_ , now that you couldn’t physically pace around in circles in your bedroom your mind was doing double time.

What if it was Dean, and he thought it was all just a mean-spirited joke? What if he thought you knew all along and had just played with him? What if he was angry? Hell, what if you walked into the damned diner only to find him, slightly disgusted tosee it was you? 

Ok, so sure, he’d always said he liked ‘her’, and it made sense if _she_ was actually you, in that case, but that didn’t make the what ifs disappear. It was terrifying, yet exhilarating. _Fuck_ , you had faced down fallen gods and the king of hell without flinching, yet the thought of meeting a _human_ man in a freaking diner had you sweating bullets.

Damn it, maybe you should have just said you were headed to the exact same place, to hunt the same damned monster. Maybe you should have played it off as a coincidence. 

Just been really freaking ditsy about it and said something like “Oh That’s _exactly_ where we’re heading! I’ll be! What a fucking coinky-dink!” Sure, it would have made you sound like an airhead. But at least then you wouldn’t be fearing the worst as the Impala slowly but surely brought you towards your own heartbreak.

What if he thought you kept it from him knowingly just to laugh at him behind his back? Why had you thought not telling him where you were going was a good idea? What stupid, shortsighted ghost had possessed you into thinking _that_ was the best thing to do in that situation? You were an idiot, and a coward. 

You were a cowardly idiot. Which was easily the worst type of idiot on the idiot Richter scale. 

Looking at Dean’s back as he drove you tried to picture an actually happy ending, like those in the movies the two of you made fun of yet both secretly liked. All rose coloured, slightly blurry and with cheesy music that swelled when the two leads finally got together. But nothing came to mind as you stayed stuck in the backseat and in the middle of your own stormy mind. Every possible outcome played out a little less rom-com and a lot more earth shattering end-of-the-world movie, sans the aliens. 

Yeah, you were thoroughly fucked. And just like every other time you screwed yourself over, it was not in the good way… Less rock your world and more tear it to fucking pieces.

 _Shit!_

Your own mind was a worse threat to you that the damned overgrown vicious pups you were out to hunt. You had to stop the mental self torment. You _needed_ to sleep for a while, or more than a while. Before you actually burned a literal hole through Dean’s back or at least singed the seat a little. 

In a vain attempt to get more comfortable you let your head hit the back of your seat with a dull thud camouflaged from the Winchester boys by Dean’s music. Sleep most likely wouldn’t come easy. You’d barely managed to keep still until you were forced to do so by the car. Yet, sleeping was better than letting your mind burn endless circles into your brain.

Maybe a bit of shut eye would stop you from admonishing your poor choices and keep the what ifs at bay for a few hours of the nearly 8 hour drive. Though you highly doubted it, you still shut your eyes and did your best to will happy thoughts and fairy dust out of thin air as you let Dean’s playlist lull you into a restless sleep. 

—

You stopped to look at yourself in the reflection of a closed window display. 

Knowing that the diner in question was just around the corner, the window stop primping was more of a strategical, cowardly attempt to buy yourself more time than actually checkin’ if everything still looked alright after the barely two block walk. The day, and time, of the meeting was finally here. Or, D-day, as you’d affectionately started calling the day in your still frenzied mind. 

As in, D for Dean and D for absolute _fucking_ disaster…

You rolled your eyes at your own mirror image at the thought of the dull joke. J.T, or Dean you guessed, had been right when he’d called you a damned comedic genius. If all else failed you could hit an open mic night and let the people there laugh at the awful mess you’d made of absolutely everything. 

Patting down your (Y/H/C) hair with shaky hands you tried, and failed, to once more push away the what ifs that plagued your mind as you gave yourself a quick once-over in the display window. Since you’d already stopped, you at least had to put an effort into making yourself believe you weren’t just being a coward. Like all those self help books said, it was all about state of mind and believing in yourself. 

Including your pathetic lies .

You’d dressed pretty inconspicuously. Your black skinny jeans were the nicest pair you owned, but they didn’t scream date or anything. And your top was just on the south side of feminine. 

Still casual enough to be something you just threw on, but nice enough to not make you look like as much of a wreck as you were feeling like. Though the outfit looked like something you just decided at random to wear you’d actually spent hours deciding on it when packing. Which you basically never did. And even then you weren’t sure it was the right choice. 

_Too late now (Y/N), you made your bed, now go fucking sleep in it._

Your reflection’s forehead creased as you silently admonished yourself and willed yourself to start walking again on heavy, boot covered feet. Looking at your watch you saw you were a few minutes late. And though you dreaded the meeting, you couldn’t make yourself ditch Dean and leave him sitting alone in the diner.

You were pretty sure it was him now. Not 100% of course, but _pretty sure_. Especially since he had said he’d be out of the motel most of the day… Still, that thought didn’t make the last stretch of your walk any easier.

Each step closer to the small diner was punctuated with another “what if” travelling from your legs up into your stomach and ending as a heavy heart beat disguised as another awful ending. 

Each step, each beat and each possible outcome was worse than the one before it as you willed yourself to keep walking until the red window sign of the small place entered your line of sight. That was your last chance, you could still turn around…

Yet, the lie fell short even before it really entered your mind. T

here was no way you could leave and let him sit there and wait for you to show up. Even though you felt like a coward, your pride wouldn’t allow you to take a coward’s way out when it came to this. 

Most, if not all, of the possible outcomes sucked… Sure. But the thought of what could possibly be the man you loved sitting, looking dejected over a cup of coffee and a slice of pie was even worse. You were a cynical coward, not a heartless monster. 

There was a difference, not much of a difference at that exact moment, but still a difference.

Using the image of a dejected Dean as fuel you forced yourself to keep walking until you could see the people inside the diner through the large front window. You spent no more than two seconds, scanning the small crowd in the diner, before you found him. Your heart playacting at being a circus acrobat as it flipped and spun in your chest.

It was him, Dean Winchester. 

The adorable fool was even wearing a Warrant band t-shirt where he sat, looking slightly nervous and out of place as he played with his coffee cup. Sure, it could still just be that the hunter just really liked the pie in the diner or something, but you doubted it. Not only was it too much of a coincidence on top of everything else, but no one else in the small sleepy diner had the look of a hunter. It _had_ to be him.

This was it, everything would most likely come crashing down around you, but you had to go through with it. This would be your judgement day. 

Seeing Dean nervously waiting in the diner through the window only solidified the fact that you _had_ to do this. He was wearing a damned band t-shirt associated with your online nickname for Christ sake, Taking a deep breath you reached out and, with shaky hands, pushed open the door. Fully aware that the minute you did so the bell above the door would ring out and Dean would look up and see you there.

Just the kind of big, grand entrance you really didn’t need on top of everything else. Nothing like an obnoxious bell to warn people about what was hiding behind door number two and set all eyes on you the minute you stepped inside.

—

Just as you knew he would, Dean’s eyes shot up to look in your direction as soon as you opened the door and the little bell rang out signaling your arrival. The cautious, yet hopeful look in his eyes proving to you that he had done the same several times only to be disappointed and return to his ongoing staring competition with his coffee cup. 

Still, this time his eyes stayed on you as he watched you with an expression that was somewhat a cross of quizzical and a deer caught in headlights. A confused deer? _Hell_ , close enough.

Raising one eyebrow he silently asked you why you were there across the busy diner floor as you took as deep a breath as possible without seeming unnatural and began the torturous trek across the linoleum flooring of the diner. A walk that, though it was technically only a few steps, seemed long and nightmarish enough to warrant a full documentary voiced by Morgan Freeman himself. Everything pointed in the direction of this being the most awkward and hellish conversation you’d ever had with the older hunter. 

_Fun_.

Still, judging by Dean’s questioning look as you reached his table, he hadn’t guessed _why_ you were actually there yet. You stood still for a second, willing yourself to talk through the sudden case of cotton-mouth you’d developed on the short walk over. 

Your reaction, and his, leading to a sort of strange stand-off that caused the old couple two tables down to look curiously in your direction. Which in turn prompted you to take an awkward and clumsy seat across from Dean.

“Hi,” 

You barely even managed to force the weak greeting out as you sat down and let your eyes fall on the cup of coffee in the hunter’s hands to avoid seeing the outrage or disappointment you were sure would soon cloud those forest green eyes you loved so much. So, in reality, you’d just greeted cooling caffeine instead of the man you loved. 

You were clearly a natural at this whole ‘don’t make things seem fucking awkward and play it cool’ thing. It was a mystery you still hadn’t received an Oscar for your amazing portrayal of what a totally normal person, _shouldn’t_ , act like. But hey, no need to worry… 

It was probably just lost in the post together with your dignity and courage.

“Hey, what are you doing here?” Dean sounded nothing but confused, and possibly a little sheepish, as if he was a kid who’d been caught with his hand in the cookie jar. 

“I mean… It’s not like you can’t be here. I was just. Uhm… I went for a walk and stopped in here for a coffee,” He added sheepishly. 

If you hadn’t known exactly why he was there you would’ve still found his words slightly incriminating. Dean had never been a good liar when it came to lying to Sammy or you. His honesty, not matter how harsh it could be at times, was part of why you loved him. And possibly part of what would soon end up crushing your heart to dust. 

Everything worth having in your life was a dual-edged sword with sharpened edges dripping in poison and pain.

Even though you were pretty much sure and ninety-nine percent certain that Dean was in fact J.T… His words still made you hesitate to come straight out and drop the bomb of why you were there and whom you were. _Shit,_ you really were a coward. If the baddies could only see you now they wouldn’t fear you all that much anymore. You were as fearsome and threatening as a kitten seeing its own reflection for the first time.

“I’m…” You stopped to clear your throat and tried to inconspicuously wipe your slightly damp palms off on your thighs, feeling your boot covered foot nervously tapping against the linoleum as you attempted to force yourself to come clean.

“I’m here to meet someone, actually,” Your words came out just a tiny bit faster and more jumbled up that you’d wanted them to be. Still, though it wasn’t as much of a straight up admission of who you actually were as you’d planned, you decided to count it as a win.

Your eyes stayed glued to the coffee cup on the table as you waited for Dean to say something, anything, back. The silence dragged on as the hunter connected two and two in front of you. Yet, you kept quiet, your hands in balled fists against your thighs as you waited for everything to explode.

You’d surely fucked everything up. 

He probably hated you, or felt betrayed. You didn’t even dare to look up in case he was looking at you in disgust. You’d never missed your computer screen as much as you did at that moment. Oh, how you longed for a screen and keyboard to hide behind. 

Technology really made makin’ a fool out of yourself easier and a fraction less painful. At least if you’d been chatting on the website you could’ve pretended the extended silence was due to a shitty WiFi connection or something…

Yeah, you were _screwed_. 

The silence was dragging on for an uncomfortable amount of time as you tried to will your leg to stop its tapping against the linoleum, and failing miserably. ‘Cause of course the universe couldn’t even let you have that one tiny thing go right. You could feel Dean’s eyes on you, almost as if every nerve in your body had betrayed you and redirected their energy to exactly where his gaze landed on you. 

Damn you and your traitorous nervous system..

Was he disappointed? Angry? Damn it, the silence was killing you more than the last few days of waiting had. You felt your eyes burn with unshed, unwanted tears that you forced back with a shaky breath. Yeah, you were definitely a reverse King Midas, everything you touched turned to shit, and now the man you’d loved for years would end up hating you.

 _Damn it,_ up until that moment you’d been unable to worry about anything further away than the actual meeting, but now that you were left sitting there… Waiting for him to speak, endless futures kept flashing to your mind as if a small piece of you were dying. 

Maybe he’d ask you to leave the bunker, or at least never joke around with you like before.

You could feel a small headache starting to form behind your eyes as you continued to experience a mirrored version of the flashbacks people said you were supposed to experience at the moment of death. Just seeing all the futures you’d possibly doomed yourself to instead of all your past happy moments. 

The silence at your table had the elderly couple a few tables down once more staring your way. You couldn’t really see them, but your heightened senses from years of hunting could still tell their murmured curiosity and looks were aimed in your direction. Treating your inevitable heartbreak as some stupid reality show.

To them you probably looked like a kid being scolded, or a girlfriend caught doing something she shouldn’t. Though you feared that when the silence broke it would do so with an explosive bang that would let the whole diner know what had happened. T.S Eliot most likely got it wrong in your case, your world, or at least your heart, would probably end with a bang, not a whimper.

“Wait…” Dean’s first words were tentative and quiet, not really giving you an insight into his emotions as he finally broke the silence. 

“Are you… I mean, you can’t be, can you? Cherry?” His voice was low, but more filled with tentative confusion than the anger you’d been expecting when he finally put two and two together and asked you the question you’d been dreading.

Maybe he just didn’t want to believe it. Maybe he still thought it was all just a whole mess of coincidences. _Hell,_ you didn’t know, but you did know you couldn’t keep dragging the whole mess out. You had to do it quickly. Like pulling off a band-aid. 

Still, you didn’t trust your voice. So you settled for a meek nod that was less ripping off the band-aid and more tugging at it before giving up and chickening out. Leaving you doomed to a half-loose band-aid existence and your eyes still glued to the untouched coffee cup on Dean’s side of the table.

“Wow, I mean… Ok,” Dean’s voice was still surprisingly calm as he spoke. Nothing like the nightmarish reactions you’d played over and over again in your mind as the meeting time approached. Which of course could just be temporary. The metaphorical calm before the shit storm hit. 

“Uhm… So how long have you… Y’know… Known?” Instead of mad, Dean sounded almost shy and maybe just slightly confused as he kept his voice at that low murmur that normally sent pleasurable chills down your back.

“Not long, I just… I guessed when you said where you were going to hunt…” Your words died out as you started speaking. The excuse sounding weak even to your own ears.

“Yeah, since it’s where we were headed too,” Dean said in agreement, as if your stupid cowardly excuse actually made sense in some weird way. But you knew he could still just be getting the facts together and you wouldn’t allow yourself to hope it was anything more than that. 

“And then you agreed to meet me, but you didn’t tell me you were hunting here too,”

And there it was… The decision you regretted the most. Damn it, not telling him had been a stupid and cowardly move to make. You just… 

You’d been protecting yourself, worried about guessing wrong and ending up inadvertently confessing more than you’d ever meant to confess to Dean.

“I was… I guess I was afraid it was all just a big coincidence. That you weren’t, y’know you,” You said to the by now probably cold coffee in front of Dean, still not brave enough to look up at him. 

“And I didn’t know how to break it to you… I’m sorry,” You added, your apology sounding weak even in your own ears as you let your nails dig into your palms to keep yourself from crying prematurely of what was probably an inevitable heartbreak. 

You’d somehow fallen in love with two men who turned out to be the same man, and now you were about to get your heart broken twice over in one go. Hell. at least you went all out when you fucked up your life. Even signing up for the newsletters and the two for one deals and shit. 

“You don’t have to be sorry… I mean… I guess it would have been a hard one to share. I’m more just…. I mean, wow,” Dean’s jumbled words made little to no sense to you. Forcing you to actually glance up at the man in front of you and meeting bright green eyes that had no trace of anger in them.

“You’re not angry?” The words left you as barely a whisper as you finally let yourself look at the man in front of you. Dean’s features morphing from mild confusion to a small smile as he looked at you.

“No I’m not angry. I’m just…” Dean lifted a hand from the table to rub the back of his neck, like he often did when he was a bit embarrassed or shy. 

“This is a lot harder than typing stuff out… I mean,”

“Yeah, I miss my keyboard too,” You sighed, your words teasing a small shy smile out of Dean before his eyes seemed to temporarily harden with determination. As if he had mentally reached some conclusion during your dull, weak joke.

“This isn’t easy to say, but I guess you’ve already kinda guessed,“ Dean took a deep breath that betrayed the shaky undertone of his own voice before continuing. His hand staying at the back of his neck as he spoke. 

“There were so many nights where I wished that you and Cherry, Cherry and you… That the two of you were the same person,” Dean’s confession teased a small awkward coughed laugh out of the big guy and that time he was the one to look down at his coffee cup. Refusing to meet your eyes.

“I guess I know what you mean… I did the same thing,” You said, finally allowing yourself to feel a bit hopeful, though still awkward as hell as you spoke more to his slightly messy hair than him. Since his eyes were now the ones locked with his cooling coffee. 

“Wishing that J.T and you were the same person I mean,” You added through the nerves that tried to stop you from vocalizing the confession. 

Damn it, why was it so easy to type things out on a computer, but so hard to say them to his face? Especially with your own heart beating so hard you could barely hear your own words as they left you. If it started beating any harder you’d need subtitles. 

The damned muscle should stop getting involved in every little thing like an overbearing helicopter mom and just fucking pump blood. That was the son of a bitch’s job after all.

“What? So _I’m_ him?” Dean finally looked up at your words, though the question that left him was not what you had expected. His bright eyes looked even brighter as they met yours with tentative hope and happiness. For a second you met his look with a confused look of your own. Your roles reversed as you were the one left trying to put two and two together, though, unlike you, Dean was more than happy to help you connect the dots. 

“I mean. Him isn’t Sammy? It’s me?” 

“Wait, wha… Oh god no. I love Sammy, but like a brother,” Your words were followed by a surprised laugh as you realised what Dean had been hinting at. Dean still looked somewhat confused and uncertain as you shook your head. 

“Sam’s just my friend Dean, my best friend, that’s all,” You said, clarifying the point as much as you possibly could.

“Then…” Dean stopped to take a sip of his coffee before putting it down with an obvious grimace once he realised how cold it had gotten in the short time your conversation had lasted. 

“It’s me?” Dean’s tentative question seemed almost fearful and damn if that wasn’t the cutest freaking thing ever. Cute enough to somehow give you the courage that had constantly been nowhere to be found ever since you fell for the hunter.

“Yeah… I mean, I’m in love with you Dean,” Your voice still wavered as you finally confessed feelings you had promised yourself you would never voice. But, in an act of treason against your own heart, you still said them. You still poured your heart out and offered it to the older hunter, hoping he would accept it, even with a few dents in the packaging.

“Wow… Wait… So I was jealous of myself all along? That’s some daytime TV shit right there. Still though… Wow,” Your not so unknown online stranger fell over his words across from you, laughter mixing into every syllable, as if he couldn’t contain his happiness. Your J.T was Dean, _your_ Dean. And he wasn’t pissed at you. He was happy, and honestly way hotter than the Chris Gyllenhaal mix in your head. 

Dean’s smile grew brighter as he finally reached out to you. His shaking fingers brushing a stray strand of (Y/H/C) hair away from your forehead. As if he was just double checking that you were really there. 

“I… Wow. I mean that’s… This is awesome,” He finally grinned, a mischievous glint in his eyes as he knew the reaction you would have to his choice of words.

“Dean!” You groaned as you rolled your eyes at him, though you couldn’t help, but smile. 

“Not everything is awesome you know,” You added, raising a hand to slap lightly at his on the table, only to have him catch yours in his own. His fingers intertwined with yours across the table whilst his eyes stayed locked with your (Y/E/C) ones, looking as mesmerized by you as you were by him.

“Maybe not everything. But this is definitely up there,” His voice still held that slight laugh, but it was softer as he smiled and squeezed your hand in his. His thumb drawing small circles on your skin as he used his hold on your hand to pull you a tiny bit closer to him across the table. 

“I’m in love with you too (Y/N),” The whispered words barely left Dean before his lips brushed against yours in a chaste, sneaky kiss that even the curious elderly couple two tables down seemed to miss. His brow furrowing momentarily in worry until you gave him a small shaky smile back to tell him the kiss was alright, hell it was more than alright.

“But… How about we keep this whole story under wraps. As in… We don’t tell Sammy about the chatting?” Dean asked, still holding you close by your hand. His voice a conspiratorial whisper as he smiled that adorably wicked half smile of his and winked your way.

“Oh God yes. I don’t think I could handle his I told you so’s,” You groaned in laughter, which was quickly cut off as Dean sealed your little promise with another soft and short, yet mind numbingly sweet, kiss. Damn, you were for once really thankful to chats and the pleasures of the internet…

Though the real world definitely had its perks too.


End file.
